Hydrochloric Acid → 6,7-dihydro-5H-dibenzo[a,c]-cyclohepten-4-carboxamide

HRID 1982620Notes

Reaction equation

HRID 1982620 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([C:16]#[N:17])=[CH:3][CH:2]=1.Cl.C([OH:21])C>[OH-].[Na+]>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([C:16]([NH2:17])=[O:21])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 132813406,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile

Product 1

HCID 133912786,7-dihydro-5H-dibenzo[a,c]-cyclohepten-4-carboxamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Under a dry nitrogen atmosphere a stirred mixture of 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile (1.0 gram, 0.0045 mole) in ethanol (20 ml) and 10% aqueous sodium hydroxide (20 ml) was heated at reflux for two days. The mixture was cooled and poured into dilute hydrochloric acid (150 ml). The resulting mixture was extracted with five 100 ml portions of methylene chloride and the extracts combined. The combined extracts were washed with two 100 ml portions of water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the filtrate by distillation under reduced pressure to leave 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carboxamide as a white solid (1.1 grams, mp>250°).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. temperatureThe mixture was cooled
  4. extractionThe resulting mixture was extracted with five 100 ml portions of methylene chloride
  5. washThe combined extracts were washed with two 100 ml portions of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate by distillation under reduced pressure

Sources & evidence

ORD record
ord-a6e00892cbd64a2aadd21ad30add1fa5
Source dataset
uspto-grants-1986_06
Patent number
US04596892

Reaction notes

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