Hydrochloric Acid → HCID 12270278, compound

HRID 1579895Notes

Reaction equation

HRID 1579895 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([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][C:6]=1[C:26]([OH:28])=[O:27])(=O)C.C(O)C.Cl>O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([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:7][C:6]=1[C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12270277HCID 12270277, compound

Product 1

HCID 12270278HCID 12270278, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g. (0.011 mole) of 1-(4-acetamido-3-carboxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole, 50 ml. of ethanol, 10 ml. of water, and 2 ml. of conc. hydrochloric acid was heated under reflux under nitrogen for 4 hours, concentrated to 10 ml., diluted with 100 ml. of water, adjusted to pH 4 and filtered. Recrystallization of the collected solid from 75% ethanol gave 0.83 g. (23%) of crystals, m.p. 205.5°-206.5°.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureunder reflux under nitrogen for 4 hours
  3. concentrationconcentrated to 10 ml
  4. addition, diluted with 100 ml
  5. filtrationfiltered
  6. customRecrystallization of the collected solid from 75% ethanol
  7. customgave 0.83 g

Sources & evidence

ORD record
ord-588f3f151bc0476397fed8a82d827ac2
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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