4-Amino-3-chlorophenol → 4-(4-Amino-2-chlorophenoxy)picolinamide

HRID 658475Notes

Reaction equation

HRID 658475 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=[O:14])[CH:8]=2)=[CH:4][C:3]=1Cl.NC1C=CC(O)=CC=1[Cl:27]>>[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=[O:14])[CH:8]=2)=[C:4]([Cl:27])[CH:3]=1

Participants

3

Reactant 2

HCID 871844-Amino-3-chlorophenolHCID 231535844-(4-Amino-3-chlorophenoxy)picolinamide

Product 1

HCID 435176714-(4-Amino-2-chlorophenoxy)picolinamide

Procedure

The title compound was prepared in the same manner described for 4-(4-amino-3-chloro-phenoxy)pyridine-2-carboxamide, substituting 4-aminophenol for 4-amino-3-chlorophenol. 1H-NMR (DMSO-d6) δ 8.43 (d, J=5.7 Hz, 1H), 8.07 (broad s, 1H), 7.66 (broad s, 1H), 7.31 (d, J=2.7 Hz, 1H), 7.07 (dd, J=5.7 Hz, 2.7 Hz, 1H), 6.85 (d, J=9.0 Hz, 2H), 6.62 (d, J=8.7 Hz, 2H), 5.17 (broad s, 2H).

Sources & evidence

ORD record
ord-efdb938fb5914248ac6952f9dacc0ec6
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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