Sodium Hydroxide → HCID 19761442, compound

HRID 373836Notes

Reaction equation

HRID 373836 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][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2.[OH-].[Na+]>C(O)(=O)C>[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]=[C:17]([O:21][CH3:22])[CH:18]=2)[NH:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 19761414HCID 19761414, compound

Product 1

HCID 19761442HCID 19761442, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (19.30 g) was added portionwise to a solution of 20.50 g 2-(2-aminophenyl)-5-methoxy-1H-indole in 1500 ml acetic acid 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 ethyl acetate, and the extracts were washed with saturated NaCl solution and dried (MgSO4). Concentration yielded 20.56 g solid. Purification of a 10 g portion by HPLC yielded 2.33 g solid, m.p. 94°-98° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-63337f55af704a44b418949e95dc3445
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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