Sodium Hydroxide → HCID 19761428, compound

HRID 373839Notes

Reaction equation

HRID 373839 reaction equation
C([BH3-])#N.[Na+].[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2.[OH-].[Na+]>CC(O)=O>[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 19761437HCID 19761437, compound

Product 1

HCID 19761428HCID 19761428, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (4.72 g) was added portionwise to a solution of 5.36 g 2-(2-methylamino-5-chlorophenyl)-1H-indole in 160 ml HOAc at 10° C. The mixture was stirred twenty hours at room temperature. It was then diluted and added to excess 50% NaOH in ice. The mixture was extracted with CH2Cl2, and the extracts were washed with saturated NaCl solution and dried (MgSO4). Concentration yielded 5.31 g solid. Purification by HPLC using CH2Cl2 /hexane (1:1) as eluent yielded 2.65 g solid, m.p. 106°-108° C.

Workup

  1. additionIt was then diluted
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe extracts were washed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-0330532eac5b452f915e7399c125b0f9
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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