5-Amino-2-chlorobenzoic acid → 2-Chloro-5-(4-Cyano-Benzoylamino)-Benzoic Acid

HRID 1662814Notes

Reaction equation

HRID 1662814 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)#[N:13]>C1COCC1>[Cl:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 607484272-Chloro-5-(4-Cyano-Benzoylamino)-Benzoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-chloro-benzoic acid (0.355 g, 2.06 mmol) was diluted with THF (12 mL), treated with 4-cyano-benzoyl chloride (0.377 g, 2.23 mmol) and stirred for 72 h. Solvents were then removed and resulting solids were triturated with DCM. After filtration, the title compound was obtained as a white solid (0.6 g, 97%).

Workup

  1. customSolvents were then removed
  2. customresulting solids
  3. customwere triturated with DCM
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-f5b7794160d14899ba4fcf13d437241c
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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