4-Aminophenol → HCID 67399933, compound

HRID 450428Notes

Reaction equation

HRID 450428 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[C:11]([O:15][C:16]([C:18]1[CH:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[CH:20][N:19]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 24758Sodium hydrideHCID 11806045tert-Butyl 4-chloropicolinate

Product 1

HCID 67399933HCID 67399933, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-aminophenol (2.6 g, 24 mmol) and NaH (1.1 g, 28 mmol) in dry DMF (50 ml) was stirred at RT for 30 min. 4-Chloro-pyridine-2-carboxylic acid t-butyl ester (5.0 g, 24 mmol) was added and the resulting mixture was stirred in a sealed tube at 80° C. for 12 h. The reaction mixture was concentrated in vacuo and was purified on silica gel to give 5-(4-amino-phenoxy)-pyridine-2-carboxylic acid t-butyl ester as a yellow solid (2.4 g, 35% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.48 (d, J=5.7 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.03 (m, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 5.18 (s, 2H), 1.50 (s, 9H); MS (ESI) m/z: 287.2 (M+H+).

Workup

  1. stirringthe resulting mixture was stirred in a sealed tube at 80° C. for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customwas purified on silica gel

Sources & evidence

ORD record
ord-90624d10967a41578c54a7f3134fece4
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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