Methanol → HCID 12270317, compound

HRID 1579879Notes

Reaction equation

HRID 1579879 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[CH:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2].[CH3:30]O>>[OH:10][C:9]1[CH:8]=[CH:7][C:6]([N:11]2[C:19]3[CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[CH:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][C:4]=1[C:1]([O:3][CH3:30])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 40821Fendosal

Product 1

HCID 12270317HCID 12270317, compound

Procedure

Hydrogen chloride gas was bubbled through a stirred, boiling mixture of 30.0 g. (0.08 mole) of 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole and 790 ml. of methanol for 1 hour. The mixture was stirred under reflux for 6 hours, cooled and filtered to provide 28.4 g. (91%) of solid. Recrystallization from acetonitrile gave colorless crystals, m.p. 164.5°-165.5°.

Workup

  1. customHydrogen chloride gas was bubbled through a stirred
  2. additionmixture of 30.0 g
  3. temperatureunder reflux for 6 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customto provide 28.4 g
  7. customRecrystallization from acetonitrile
  8. customgave colorless crystals, m.p. 164.5°-165.5°

Sources & evidence

ORD record
ord-56b17bd9902a43199ccb5b1c51766b4d
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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