Hydrazine hydrate (1:1) → HCID 12752373, compound

HRID 2164069Notes

Reaction equation

HRID 2164069 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6].[OH2:15].NN>C(O)C.[Ni]>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([N:2]([CH3:14])[CH3:1])[C:4]=1[C:5]([NH2:6])=[O:15]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11535716Benzonitrile, 2-(dimethylamino)-6-nitro-

Product 1

HCID 12752373HCID 12752373, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

2-Amino-6-dimethylaminobenzamide is prepared by adding a suspension of 2-dimethylamino-6-nitrobenzonitrile and hydrazine hydrate in ethanol to a suspension of Raney nickel in ethanol while maintaining the reaction temperature at about 65° C. The mixture is then heated to reflux for about half an hour, filtered through Celite and evaporated to dryness. The solid product may be recrystallized from ethanol or used neat in the reaction with ethyl oxalyl chloride.

Workup

  1. additionby adding
  2. temperatureThe mixture is then heated
  3. temperatureto reflux for about half an hour
  4. filtrationfiltered through Celite
  5. customevaporated to dryness
  6. customThe solid product may be recrystallized from ethanol
  7. customused neat in the reaction with ethyl oxalyl chloride

Sources & evidence

ORD record
ord-b0cccec433684ae59b3dcb738f7c0145
Source dataset
uspto-grants-1979_01
Patent number
US04137325

Reaction notes

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