4-Chloro-o-anisic acid → HCID 62803697, compound

HRID 1875746Notes

Reaction equation

HRID 1875746 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([NH2:22])[C:17]([NH2:21])=[CH:18][C:19]=1[F:20]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[NH:21][C:17]3[CH:18]=[C:19]([F:20])[C:14]([F:13])=[CH:15][C:16]=3[N:22]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

3

Reactant 2

HCID 936824-Chloro-o-anisic acidHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 62803697HCID 62803697, compoundYield 77%

Conditions

Temperature
180 °C

Procedure

To a suspension of 4-chloro-2-methoxy-benzoic acid (5 g, 0.026 mol; CAS Reg. No. 78955-90-5) in polyphosphoric acid (50 g) was added compound 4,5-difluoro-benzene-1,2-diamine (3.86 g, 0.026 mol; CAS Reg. No. 76179-40-3) and the resulting mixture was heated to 180° C. for 1 h. The reaction mixture was then cooled and neutralized with ice cold 10% aqueous sodium carbonate solution, and then extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (25% ethyl acetate/n-hexane) to give the desired compound as a brown solid (77%). MS (Turbo Spray): m/z=295.1 (M+H).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel (25% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-9be4d96cd1624a7eb2efb5f015602256
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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