Ammonia → HCID 22763455, compound

HRID 1973037Notes

Reaction equation

HRID 1973037 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].Cl.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

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 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 mol) 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 half an hour and cooled to room temperature. 5 ml of 5N aqueous HCl 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 half an hour
  2. temperaturecooled to room temperature
  3. temperaturethe mixture is refluxed for 20 minutes
  4. extractionthe precipitate is extracted with chloroform
  5. washThe chloroform layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customRecrystallization from chloroform (charcoal)
  10. customaffords colorless crystals

Sources & evidence

ORD record
ord-1d9343f26b9142109ea896eced740d60
Source dataset
uspto-grants-1976_12
Patent number
US03996159

Reaction notes

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