Hydrochloric Acid → HCID 21318141, compound

HRID 263064Notes

Reaction equation

HRID 263064 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]#[N:15])=[C:8]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:4].Cl.C(C1(C(O)=O)C(C2C=CC=CC=2)=C2C(C=CC=C2)=N1)#N>C(O)C>[C:14]([C:9]1[NH:10][C:11]2[C:7]([C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=2)#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21318143HCID 21318143, compoundHCID 54350301HCID 54350301, compound2×

Product 1

HCID 21318141HCID 21318141, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1.50 g. (5.4 mmol) of 2-cyano-3-phenylindole-5-carboxylic acid methyl ester in 50 ml. of 6 N hydrochloric acid was heated under reflux, enough ethanol (~ 100 ml.) was added to effect solution, and heating was continued for 11 days. The reaction was concentrated to a small volume under vacuum, diluted with water and made basic with sodium hydroxide. Filtration gave 840 mg. of recovered 2-cyano-3-phenylindole-5-carboxylic acid methyl ester. The basic solution was acidified, the amorphous precipitate was collected by filtration and recrystallized four times from methanol with charcoal to give 111 mg. (19%) of 2-cyano-3-phenylindole-2-carboxylic acid as colorless crystals, m.p. 302°-304°.

Workup

  1. additionA suspension of 1.50 g
  2. temperatureunder reflux
  3. temperatureheating
  4. concentrationThe reaction was concentrated to a small volume under vacuum
  5. additiondiluted with water
  6. filtrationFiltration
  7. customgave 840 mg
  8. filtrationthe amorphous precipitate was collected by filtration
  9. customrecrystallized four times from methanol with charcoal
  10. customto give 111 mg

Sources & evidence

ORD record
ord-c5d290e5e13241b6836c22cffe182d39
Source dataset
uspto-grants-1979_05
Patent number
US04156016

Reaction notes

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