O-Toluidine → (2-Chloro-4-o-tolylamino-phenyl)-(2-methyl-5-nitro-phenyl)-methanone

HRID 2067210Notes

Reaction equation

HRID 2067210 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12](C(F)(F)F)=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20].Br[C:32]1C=CC(C(C2C=C([N+]([O-])=O)C=CC=2C)=O)=C(Cl)C=1.CC1C=CC=CC=1N>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:32])[CH:5]=[CH:4][C:3]=1[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH3:30])=[O:20]

Participants

4

Reactant 3

HCID 7242O-ToluidineHCID 11494123(4-Bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanoneHCID 68419760[2-Chloro-4-(4-trifluoromethyl-phenylamino)-phenyl]-(2-methyl-5-nitro-phenyl)-methanone

Product 1

HCID 68418373(2-Chloro-4-o-tolylamino-phenyl)-(2-methyl-5-nitro-phenyl)-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 414, using compound 402 (0.28 mmol) and 2-methyl aniline (0.28 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/EtOAc 0:100 to 25:75 as the eluent to afford the title compound as yellow foam.

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-9fc57ffecb364231ae3f4bfd9a2705b7
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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