Sodium Hydroxide → 5-Amino-2-chloro-N-methylbenzamide

HRID 1435746Notes

Reaction equation

HRID 1435746 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Sn](Cl)Cl.[OH-].[Na+]>Cl>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 27951452-chloro-N-methyl-5-nitrobenzamide

Product 1

HCID 167723205-Amino-2-chloro-N-methylbenzamideYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a suspension of 2-chloro-N-methyl-5-nitro-benzamide (2.3 mmol) in concentrated hydrochloric acid (3 ml) was added a solution of tin dichloride (1.4 g, 7.2 mmol) in concentrated hydrochloric acid (4 ml). After stirring for 20 hours, the mixture was cooled in an ice bath and treated with 50% sodium hydroxide to basic pH. The mixture was extracted with ethyl acetate (3×25 ml). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure to provide 5-amino-2-chloro-N-methylbenzamide (274 mg, 88% yield).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionThe mixture was extracted with ethyl acetate (3×25 ml)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39d36e5fafbb429b82a493eba86e0142
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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