4-Chloro-2-nitrobenzoic acid → HCID 67050100, compound

HRID 1875840Notes

Reaction equation

HRID 1875840 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=O)=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1>CC1C=CC=CC=1C.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]2[NH:9][C:5]3[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=3[N:10]=2)=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1

Participants

5

Reactant 2

HCID 804754-Chloro-2-nitrobenzoic acidHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 67050100HCID 67050100, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 7237O-XyleneSolvent

Procedure

To a solution of 4,5-difluoro-benzene-1,2-diamine (2.0 g, 6.94 mmol; CAS Reg. No. 76179-40-3) in o-xylene (25 ml) was added 4-chloro-2-nitro-benzoic acid (2.78 g, 6.94 mmol; CAS Reg. No. 6280-88-2) and titanium tetraethoxide (2.9 ml, 6.94 mmol) at 25° C., and the reaction mixture was allowed to stir at reflux temperature for 14 h. After the completion of reaction, solvents were evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (18-20% ethyl acetate/n-hexane) to afford the desired compound as a yellow powder (15%). MS (Turbo Spray): m/z=310.2 (M+H).

Workup

  1. customat 25° C.
  2. temperatureat reflux temperature for 14 h
  3. customAfter the completion of reaction, solvents
  4. customwere evaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (18-20% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-170b498dbd7c4c50809ae68191d7181a
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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