Ammonia → HCID 22763455, compound

HRID 1112295Notes

Reaction equation

HRID 1112295 reaction equation
B.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]#[N:13])=[C:6]2[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21].N>O1CCCC1>[NH2:13][CH2:12][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21])=[CH:4][C:3]([Cl:2])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6331BoraneHCID 22763450HCID 22763450, compound

Product 1

HCID 22763455HCID 22763455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane in tetrahydrofuran (7 ml of a 1M solution) is added to a solution of 1 g (3.46 mmol) of 5-chloro-3-(2,6-difluorophenyl) indole-2-carbonitrile in 15 ml of dry tetrahydrofuran. The solution is stirred at room temperature for 2 hours and then refluxed for 1/2 and cooled to room temperature. 5 ml of 5N aqueous NCl is added dropwise and the mixture is refluxed for 20 minutes. The mixture is then poured onto a mixture of ice and aqueous 10 percent ammonia, and the precipitate is extracted with chloroform. The chloroform layer is washed with water and dried over magnesium sulfate, filtered and evaporated to dryness. Recrystallization from chloroform (charcoal) affords colorless crystals; m.p. 212°-214°.

Workup

  1. temperaturerefluxed for 1/2
  2. temperaturecooled to room temperature
  3. addition5 ml of 5N aqueous NCl is added dropwise
  4. temperaturethe mixture is refluxed for 20 minutes
  5. extractionthe precipitate is extracted with chloroform
  6. washThe chloroform layer is washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customRecrystallization from chloroform (charcoal)
  11. customaffords colorless crystals

Sources & evidence

ORD record
ord-18a045c4ccc14350a5ded393281fbf43
Source dataset
uspto-grants-1978_10
Patent number
US04122034

Reaction notes

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