Sodium Cyanide → HCID 20309106, compound

HRID 1763214Notes

Reaction equation

HRID 1763214 reaction equation
Br[C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[F:18])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.[CH3:19][N:20]1CCCC1=O.[C-]#N.[Na+]>O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:3]2[C:2]([C:19]#[N:20])=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)=[N:4]2)=[C:12]([F:18])[CH:13]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 13387N-methyl-2-pyrrolidoneHCID 20309095HCID 20309095, compound

Product 1

HCID 20309106HCID 20309106, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.7 Parts of 3-bromo-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole [from Example 1-d] was combined with 1.5 parts of cuprous cyanide in 60 parts of N-methylpyrrolidinone and heated to 190° for 2 hours. After cooling to 30°, the reaction mixture was digested in a solution of 15 parts of sodium cyanide in 150 parts of water at 65°-70° for 2 hours, then extracted with 250 parts of toluene four times. The combined toluene extracts were washed with 500 parts of water 4 times, followed by 100 parts saturated aqueous sodium chloride. After drying with anhydrous sodium sulfate, the solution was evaporated at 50° and 50 mm. Hg to yield 4.4 parts of a brown oil. After crystallization from methylcyclohexane, 1.1 parts of 2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole-3-carbonitrile melting at 83°-84° were isolated.

Workup

  1. temperatureheated to 190° for 2 hours
  2. temperatureAfter cooling to 30°
  3. extractionextracted with 250 parts of toluene four times
  4. washThe combined toluene extracts were washed with 500 parts of water 4 times
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. customthe solution was evaporated at 50°
  7. custom50 mm. Hg to yield 4.4 parts of a brown oil
  8. customAfter crystallization from methylcyclohexane, 1.1 parts of 2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole-3-carbonitrile melting at 83°-84°
  9. customwere isolated

Sources & evidence

ORD record
ord-ad682e4dba004f3194f8b3c7381df22a
Source dataset
uspto-grants-1978_09
Patent number
US04111681

Reaction notes

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