Sodium Hydroxide → HCID 9859660, compound

HRID 373835Notes

Reaction equation

HRID 373835 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.[OH-].[Na+]>CC(O)=O>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 10999214HCID 10999214, compound

Product 1

HCID 9859660HCID 9859660, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (6.37 g) was added portionwise to a solution of 7.00 g 2-(2-amino-5-chlorophenyl)-1H-indole in 245 ml HOAc at 15° C. The resulting solution was stirred at room temperature for one day. The reaction mixture was diluted and made basic by addition of 50% NaOH in ice. The mixture was extracted with Et2O, and the extracts were washed with water and saturated NaCl solution, and dried (MgSO4). Concentration gave 6.48 g gum which was chromatographed by HPLC using CH2Cl2 /hexane (7:3) as eluent to give 2.56 g solid, m.p. 107°-109° C.

Workup

  1. additionThe reaction mixture was diluted
  2. extractionThe mixture was extracted with Et2O
  3. washthe extracts were washed with water and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-3e249feeb49b4357bab84167bbde4310
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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