Ammonia → 1-(2-Hydroxyethyl)-2,3-dihydro-1H-indol-4-ol

HRID 1291937Notes

Reaction equation

HRID 1291937 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:15][CH2:16][OH:17].N>C(O)(=O)C>[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][N:10]2[CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 15413204HCID 15413204, compound

Product 1

HCID 195984631-(2-Hydroxyethyl)-2,3-dihydro-1H-indol-4-olYield 86.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.9 g of sodium cyanoborohydride were added to a solution of 8.85 g of 4-hydroxy-1-N-(β-hydroxyethyl)indole, obtained in the preceding stage, in 40 cm3 of acetic acid, the temperature being maintained below 30° C. After stirring for 30 minutes, the reaction mixture was poured onto 200 g of ice-cold water and the pH was neutralized to 7.5 by addition of 30% aqueous ammonia. The precipitate obtained was filtered off and dried. 7.75 g of 4-hydroxy-1-N-(β-hydroxyethyl)indoline were obtained, the melting point of which was 108° C. 13C and proton nuclear magnetic resonance (N.M.R.) analysis of the product obtained was found to be in accordance with the expected product.

Workup

  1. temperaturethe temperature being maintained below 30° C
  2. customThe precipitate obtained
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-548844c4e54746ff9446370422a39ae8
Source dataset
uspto-grants-1998_05
Patent number
US05755829

Reaction notes

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