Water → 2-(2-Aminophenyl)-2,3-dihydro-1H-indole

HRID 373834

Reaction equation

HRID 373834 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.O>CC(O)=O>[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 7359662-(2-Aminophenyl)indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 197614202-(2-Aminophenyl)-2,3-dihydro-1H-indoleYield 50.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (6.4 g) was added in several portions to a solution of 6.0 g 2-(2-aminophenyl)-1H-indole in 200 ml HOAc at 5° C. The resulting solution was stirred at room temperature overnight. Water was added and the reaction mixture was concentrated. The residue was diluted with ice water and made basic with 50% NaOH. This mixture was extracted with Et2O and the extracts were washed with water and saturated NaCl solution, and dried (MgSO4). Concentration gave 6.1 g crude product which was chromatographed by HPLC to give 3.05 g solid, m.p. 115°-117° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was diluted with ice water
  3. extractionThis mixture was extracted with Et2O
  4. washthe extracts were washed with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customgave 6.1 g crude product which
  8. customwas chromatographed by HPLC

Sources & evidence

ORD record
ord-39c031d9a1c24f2885879d80cceb81be
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Linked notes

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