Hydrazine → Bay-H-1127

HRID 1283704Notes

Reaction equation

HRID 1283704 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:14][NH2:15]>C(O)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:6]=2)[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 122239802-Bromo-5-(trifluoromethyl)benzonitrile

Product 1

HCID 16736Bay-H-1127

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 8.0 g. of 2-bromo-5-trifluoromethylbenzonitrile, 3 ml. of 95% hydrazine and 40 ml. of ethanol is kept at 45°-50° C. for 30 hours. The solution is evaporated to dryness. The residue is treated with 100 ml. of 2 N hydrochloric acid, then stirred and heated to 95° C. On cooling the aqueous layer is decanted off and treated with sodium acetate to near neutrality. The precipitate is isolated by filtration and recrystallized from benzene to yield 3-amino-5-trifluoromethylindazole, M.P. 122°-123° C.

Workup

  1. customThe solution is evaporated to dryness
  2. additionThe residue is treated with 100 ml
  3. temperatureOn cooling the aqueous layer
  4. customis decanted off
  5. additiontreated with sodium acetate
  6. customThe precipitate is isolated by filtration
  7. customrecrystallized from benzene

Sources & evidence

ORD record
ord-087d9cdc370b4fe0b11e7df6802d4d2a
Source dataset
uspto-grants-1976_08
Patent number
USRE028939

Reaction notes

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