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

HRID 558187
Notes
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Reaction equation

HRID 558187 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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-ac1a079beec447e19361869e314a30e0
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063049B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes