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

HRID 658474Notes

Reaction equation

HRID 658474 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-chlorophenoxy)pyridine-2-carboxamide, substituting 4-amino-2-chlorophenol for 4-amino-3-chlorophenol. 1H-NMR (DMSO-d6) 88.46 (d, J=5.7 Hz, 1H), 8.08 (s, 1H), 7.69 (s, 1H), 7.25 (d, J=2.7 Hz, 1H), 7.08 (dd, J=2.7, 5.7 Hz, 1H), 7.02 (d, J=8.4 Hz, 1H), 6.74 (d, J=2.7 Hz, 1H), 6.59 (dd, J=2.7, 8.7 Hz, 1H), 5.50 (s, 2H); MS LC-MS (MH)+=264.1, RT=1.76 min.

Sources & evidence

ORD record
ord-93de2af183624a68b51e07c67589628e
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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