Hydrochloric Acid → 3,5-Diamino-4-chlorobenzonitrile

HRID 1730674Notes

Reaction equation

HRID 1730674 reaction equation
Cl.[Cl:2][C:3]1[C:10]([N+:11]([O-])=O)=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[N+:14]([O-])=O.[OH-].[Na+]>>[Cl:2][C:3]1[C:10]([NH2:11])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[NH2:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 160084-Chloro-3,5-dinitrobenzonitrile

Product 1

HCID 124029953,5-Diamino-4-chlorobenzonitrile

Procedure

To a solution of 352.5 grams (1.56 mole) of stannous chloride dihydrate in 860 ml. of concentrated hydrochloric acid is added 50 gm. (0.2195 mole) of 4-chloro-3,5-dinitrobenzonitrile. The mixture is stirred at room temperature for 2 hours and cooled to 0° in an ice-salt bath. A cold solution of 50% sodium hydroxide is added to the mixture until strongly basic. During the addition the temperature is kept below 30°.

Workup

  1. temperaturecooled to 0° in an ice-salt bath
  2. additionDuring the addition the temperature
  3. customis kept below 30°

Sources & evidence

ORD record
ord-a6bd8ecb76a84ad4863345f944e381ae
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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