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

HRID 1373195Notes

Reaction equation

HRID 1373195 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7](F)=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23].O1CCCC1.O.[CH2:31]([NH2:34])[CH:32]=[CH2:33]>CO.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH:34][CH2:31][CH:32]=[CH2:33])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23]

Participants

7

Reactant 4

HCID 962WaterHCID 7853AllylamineHCID 8028TetrahydrofuranHCID 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 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-nitro-benzoic acid methyl ester (456.0 g, 1.008 mol) in a mixture of methanol (4.5 L), tetrahydrofuran (4.5 L) and water (1.13 L) was treated with allylamine (441.89 ml, 336.25 g, 5.88 mol) and stirred at room temperature for 30 min. (completion of reaction was confirmed by TLC-DCM:MeOH/9:1). The yellow colored suspension was filtered and washed with hexane to remove unreacted allylamine and dried to give the title compound as solid (yellow). Yield: 350g (50.90%), mp. 153–154° C.

Workup

  1. filtrationThe yellow colored suspension was filtered
  2. washwashed with hexane
  3. customto remove unreacted allylamine
  4. customdried

Sources & evidence

ORD record
ord-7a7ce787382b446d9d622df419439d78
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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