Methanol → 1-(4-Hydroxy-3-methoxycarbonylphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

HRID 1579866Notes

Reaction equation

HRID 1579866 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2].[CH3:26]O>>[OH:10][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:4]=1[C:1]([O:3][CH3:26])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 9967439HCID 9967439, compound

Product 1

HCID 122702801-(4-Hydroxy-3-methoxycarbonylphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

Procedure

Hydrogen chloride gas was bubbled through a boiling mixture of 25.0 g. (0.075 mole) of 1-(3-carboxy-4-hydroxyphenyl) 2-phenyl-4,5,6,7-tetrahydroindole and 750 ml. of methanol for 2 hours. The mixture was heated under reflux for 18.5 hours, cooled and filtered to provide 19.6 g. (75%) of white solid. Recrystallization from methanol gave colorless crystals, m.p. 141°-142°.

Workup

  1. customHydrogen chloride gas was bubbled through a boiling mixture of 25.0 g
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 18.5 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customto provide 19.6 g
  7. customRecrystallization from methanol
  8. customgave colorless crystals, m.p. 141°-142°

Sources & evidence

ORD record
ord-1add51ca11fa4468b1c1af5cc4a595c3
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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