Methanol → Methyl 4-(allylamino)-3-fluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoate

HRID 1161784Notes

Reaction equation

HRID 1161784 reaction equation
[F:1][C:2]1[C:3]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])=[C:4]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1F)[C:5]([O:7][CH3:8])=[O:6].[CH2:25]([NH2:28])[CH:26]=[CH2:27].CO.O>C1COCC1>[CH2:25]([NH:28][C:11]1[C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:2]=1[F:1])[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 7853AllylamineHCID 58781115Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

Product 1

HCID 58781109Methyl 4-(allylamino)-3-fluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoate (3.9 g, 8.62 mmoles) and allylamine (3.5 ml, 43 mmoles) in a mixture of THF (10 ml), MeOH (10 ml) and H2O (2.5 ml) is stirred at room temperature for 30 min. The yellow suspension is filtered and washed with hexane to remove the excess of allylamine. The resulting solid is dried under vacuum to obtain the title compound.

Workup

  1. filtrationThe yellow suspension is filtered
  2. washwashed with hexane
  3. customto remove the excess of allylamine
  4. customThe resulting solid is dried under vacuum

Sources & evidence

ORD record
ord-af9d7ea2af7b42e38cd680fccb76e87a
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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