Hydrochloric Acid → 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide

HRID 1641468Notes

Reaction equation

HRID 1641468 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([CH:15]=1)[C:7]([NH:9][CH:10]([CH:12]1[CH2:14][CH2:13]1)[CH3:11])=[O:8].Cl.O>C(O)C>[NH2:16][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][C:6]=1[C:7]([NH:9][CH:10]([CH:12]1[CH2:14][CH2:13]1)[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 433994465-chloro-N-(1-cyclopropylethyl)-2-nitrobenzamide

Product 1

HCID 435330962-amino-5-chloro-N-(1-cyclopropylethyl)benzamideYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.8 g of 5-chloro-N-(1-cyclopropylethyl)-2-nitrobenzamide was dissolved in 88 ml of ethanol, and 12.6 ml of concentrated hydrochloric acid was dropwise added under cooling with ice. After stirring at the same temperature for 0.5 hour, 4.0 g of reduced iron was added dividedly in several addition. After stirring at room temperature for 3 hours, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure. Hexane/ethyl acetate were added to the residue, followed by stirring, and the mixture was subjected to filtration to obtain 3.5 g of the pale yellow desired product (melting point: 135° C.).

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring at room temperature for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate, and ethyl acetate
  6. distillationwas distilled off under reduced pressure
  7. additionHexane/ethyl acetate were added to the residue
  8. stirringby stirring
  9. filtrationthe mixture was subjected to filtration

Sources & evidence

ORD record
ord-fc19fe746ac547e78f6cf6066acc1018
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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