Acetic Acid → 2-Amino-5-methoxyphenol

HRID 1965865Notes

Reaction equation

HRID 1965865 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=C(N)[O:9][C:5]=2[CH:4]=1.COC1C=CC([N+]([O-])=O)=C(O)C=1.CC(O)=O>CO.[Pd]>[NH2:7][C:6]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[OH:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2196355-Methoxy-2-nitrophenolHCID 596783776-Methoxy-1,3-benzoxazol-2-amine

Product 1

HCID 99421632-Amino-5-methoxyphenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

General experimental procedure for the preparation of 6-methoxybenzo[d]oxazol-2-amine: A mixture of 5-methoxy-2-nitrophenol (0.51 g, 3.02 mmol), Pd/C (10% by weight, 70 mg), and HOAc (cat. amount) in MeOH (30 mL) was hydrogenated under H2 at room temperature for 2 hrs, and then was filtered through a short Celite pad. The filtrate was concentrated in vacuo to provide 2-amino-5-methoxyphenol as a brown solid (0.42 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 6.79 (d, J=8.4 Hz, 1H), 6.44 (d, J=2.8 Hz, 1H), 6.35 (dd, J=8.4, 2.8 Hz, 1H), 3.74 (s, 3H). This product was used directly in the next step without any further purification.

Workup

  1. filtrationwas filtered through a short Celite pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5f755a399e164bc08bcb341c91df6637
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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