4-Aminophenol → 4-(4-Amino-3-chlorophenoxy)picolinamide

HRID 658473Notes

Reaction equation

HRID 658473 reaction equation
C[NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].NC1C=CC(O)=CC=1.CNC(C1C=C([Cl:37])C=CN=1)=O>>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH2:2])=[O:4])[CH:10]=2)=[CH:13][C:14]=1[Cl:37]

Participants

4

Reactant 3

HCID 4034-AminophenolHCID 14768144-Chloro-N-methylpicolinamideHCID 166551294-(4-Aminophenoxy)-N-methylpicolinamide

Product 1

HCID 231535844-(4-Amino-3-chlorophenoxy)picolinamide

Procedure

The title compound was prepared in the same manner described for 4-(4-aminophenoxy)pyridine-2-carboxylic acid methylamide, substituting 4-amino-3-chlorophenol for 4-aminophenol, and substituting 4-chloro-2-pyridinecarboxamide for 4-chloropyridine-2-carboxylic acid methylamide. 1H-NMR (DMSO-d6) δ 8.45 (d, J=5.4 Hz, 1H), 8.08 (s, 1H), 7.67 (s, 1H), 7.32 (d, J=2.7 Hz, 1H), 7.15 (d, J=2.7 Hz, 1H), 7.09 (dd, J=2.7, 5.4 Hz, 1H), 6.93 to 6.84 (m, 2H), 5.44 (s, 2H); MS LC-MS (M+H)+=264.1, RT=2.40 min.

Sources & evidence

ORD record
ord-9e33882198804af78ecd59171f8d6d2c
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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