Ammonia → HCID 21514240, compound

HRID 1605089Notes

Reaction equation

HRID 1605089 reaction equation
C([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21]([OH:23])=[O:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>>[CH2:19]1[C:20]2[NH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]=2[CH:16]([C:21]([OH:23])=[O:22])[CH2:17][CH2:18]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 21514274HCID 21514274, compound

Product 1

HCID 21514240HCID 21514240, compound

Procedure

To 40 g. 9-benzyl-1,2,3,4-tetrahydrocarbazole-4-carboxylic acid in one liter of liquid ammonia was added, with stirring and portionwise, 8.6 g. of sodium. Ammonium chloride was added portionwise until the blue color of the mixture was dissipated. The ammonia was evaporated, water was added and the mixture was extracted with ether. The aqueous solution was chilled and acidified with dilute hydrochloric acid and the resulting solid was collected by filtration and washed with water to give 23 g. of the title compound; m.p. 163°-165°C. (benzene-methyl alcohol).

Workup

  1. customThe ammonia was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with ether
  4. temperatureThe aqueous solution was chilled
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water
  7. customto give 23 g

Sources & evidence

ORD record
ord-53a23b40c8b6468884674f04886178d2
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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