O-Methylhydroxylamine → N-methoxy-3-(2-chloro-4-iodo-phenylamino)-isonicotinamide

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].[CH3:19][O:20][NH2:21]>>[CH3:19][O:20][NH:21][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][N:17]=[CH:18][C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[Cl:1]

Participants

Reactant 2

HCID 4113O-Methylhydroxylamine

HCID 576496513-[(2-Chloro-4-iodophenyl)amino]isonicotinic acid2×

Product 1

HCID 11589486N-methoxy-3-(2-chloro-4-iodo-phenylamino)-isonicotinamide

Procedure

N-methoxy-3-(2-chloro-4-iodo-phenylamino)-isonicotinamide was synthesized according to the procedure for General Method 1, outlined above, starting with 0.30 mmol of 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid (intermediate 2) and 0.42 mmol of O-methyl-hydroxylamine. LC/MS [8.75 min; 404 (M+1)]

Workup

customLC/MS [8.75 min; 404 (M+1)]

Sources & evidence

ORD record: ord-97e83a8c3a8e47f1a98c2fc1460c4b20
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841459B2

Reaction notes

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