Ammonia → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 1516394Notes

Reaction equation

HRID 1516394 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-])=O)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].N>C(OCC)(=O)C>[NH2:18][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21906173HCID 21906173, compound

Product 1

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamideYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 5-Chloro-N-(5-chloro-pyridin-2-yl)-2-nitro-benzamide (26 g, 0.0833 mol) in ethyl acetate (170 mL) was added Stannous chloride dihydrate (75 g, 0.333 mol) at 25-30° C. After stirring at same temperature for 2 hr, reaction mixture was diluted with 250 mL ethyl acetate and made alkaline with aqueous ammonia solution. Reaction mixture was then filtered through hyflow bed and organic layer was dried over sodium sulfate. Evaporation of solvent afforded 19 g of titled compound in 81% yield.

Workup

  1. customreaction mixture
  2. customReaction mixture
  3. filtrationwas then filtered through hyflow bed and organic layer
  4. dry with materialwas dried over sodium sulfate
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-fc11fb4cfd74471187fe1342c4bc686b
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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