Provide Structure of C10H13NO2 Given IR and NMR Data?

Question

Can someone help provide a structure for the following compound: C10H13NO2? 
Data provided:
- IR Absorptions: 3285, 1659, 1246 cm–1.
- 1H NMR Spectrum: Detailed observations below.
Here is my best guess, which turned out to be incorrect:
Link to spectrum image.
Hints provided:
1. The resonance at δ 7.6 is a broad singlet.
2. The IR absorptions suggest the presence of two functional groups, one of which is a carboxylic acid derivative.
3. The coupled quartet and triplet splittings in the NMR spectrum indicate the presence of a common alkyl group. (Remember the n+1 rule: n adjacent protons cause the resonance of an observed proton to split into n+1 lines.)
4. The aromatic splitting patterns suggest a para-substituted aromatic ring.
5. The IR data indicate the presence of a secondary amide (confirmed by the N–H bond).
Here’s what was pointed out about my incorrect attempt:
- The chemical shifts in my proposed structure don’t match the data. For example, the magnitude of the chemical shift of the quartet isn’t accounted for. N-adjacent alkyl group protons typically resonate below δ 3, and a phenolic OH resonance usually appears at δ 5–6.
- I originally thought the coupled quartet and triplet splittings indicated an ethyl group. My book suggests that phenolic OH resonances appear around δ 6–8, so I was surprised when this didn’t match up. 
- I also didn’t consider the N–H bond when I made my guess.
My initial interpretation of the IR data:
- 3285 cm–1: Possibly an OH group.
- 1659 cm–1: Indicated either a C=C double bond or a C=O double bond.
- 1246 cm–1: Suggested an sp3-hybridized C–O single bond.
Given this information, can anyone help clarify the structure or guide me on where my interpretation went wrong? Any assistance would be greatly appreciated!

Dr. Evert Nikolaus DVM · Accepted Answer

ANSWER: 
A para-substituted benzene ring (two branches on opposite sides): 
One branch is -NHC(=O)CH3 
 The other branch is -OCH2CH3

Nathanial Gulgowski

Provide Structure of C10H13NO2 Given IR and NMR Data?

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