2-Chloro-4-nitrobenzoic acid → HCID 57859273, compound

HRID 912420Notes

Reaction equation

Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[NH:18]C(=O)C>>[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:4](=[O:6])[C:3]3[C:2]([NH:18][C:17]=2[CH:16]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][CH:7]=3

Participants

Reactant 2

HCID 74482-Chloro-4-nitrobenzoic acid

HCID 7604m-Aminoacetanilide

Product 1

HCID 57859273HCID 57859273, compound

Procedure

The compound S3 (Y═NH) was prepared using 2-chloro-4-nitrobenzoic acid and 3′-aminoacetanilide in the same way as S3 (Y═O). 1H-NMR (DMSO-d6) δ 11.54 (s, 1H), 8.32 (d, J=8.8, 1H), 8.26 (d, J=2.0, 1H), 7.92 (d, J=8.8, 1H), 7.86 (d, J=2.0, 8.4, 1H), 6.60 (dd, J=2.0, 8.8, 1H), 6.43 (d, J=2.0, 1H), 6.36 (bs, 2H). ESI-MS m/z (M+H) calc'd: 256.1. found 256.1.

Workup

customThe compound S3 (Y═NH) was prepared

Sources & evidence

ORD record: ord-cd8e1097e4da4628b9738675f5249ebb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026110B2

Reaction notes

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