Hydrochloric Acid → 3,5-Diaminobenzonitrile

HRID 1278423Notes

Reaction equation

HRID 1278423 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:8]#[N:9])([O-])=O.[OH-].[Na+]>>[NH2:2][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([NH2:13])[CH:12]=1)[C:8]#[N:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20062Benzonitrile, 3,5-dinitro-

Product 1

HCID 128973293,5-Diaminobenzonitrile

Procedure

To a solution of 210 grams of stannous chloride dihydrate in 590 ml. of concentrated hydrochloric acid is added portionwise 25 grams of 3,5-dinitrobenzonitrile. The mixture is stirred for three hours at room temperature, then cooled to 0° in an ice-salt bath and a cold 50% sodium hydroxide solution added to the mixture until the mixture is strongly basic. During the addition the temperature is kept below 5°.

Workup

  1. temperaturecooled to 0° in an ice-salt bath
  2. additionDuring the addition the temperature
  3. customis kept below 5°

Sources & evidence

ORD record
ord-aecda7b3ed1247dc9f297da76bca5bc3
Source dataset
uspto-grants-1981_07
Patent number
US04281151

Reaction notes

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