Formic Acid → HCID 20523613, compound

HRID 1105732Notes

Reaction equation

HRID 1105732 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:12]=[C:11]2[C:6]=1[CH:7]1[CH2:40][C:39](=O)[CH2:38][CH2:37][CH:8]1[C:9]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:29])N2)(=O)C.C(N)=O.C(O)=O.C(=O)([O-])[O-].[NH4+:52].[NH4+:53]>O>[NH2:52][CH:39]1[CH2:38][CH2:37][CH:8]2[C:9]([CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([CH3:29])[NH:53][C:11]3[C:6]([CH:7]2[CH2:40]1)=[C:5]([OH:4])[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:12]=3

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 713FormamideHCID 517111Ammonium CarbonateHCID 20523621HCID 20523621, compound

Product 1

HCID 20523613HCID 20523613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.53 g. (0.01 mole) of dl-1-acetoxy-6-benzyl-6-methyl-3-(8-phenyl-4-thiaoctyl)-5,6,6a,7,10,10a-hexahydrobenzo[c]quinoline-9(8H)one, 5 ml. formamide and 10 ml. formic acid is heated at reflux under a nitrogen atmosphere while removing water as it forms in the reaction. Additional formic acid is added as required to control deposition of ammonium carbonate in the condenser. When the reaction temperature reaches 195° C., the mixture is cooled, diluted with water and extracted with ethyl acetate. The extract is evaporated to dryness, 5 ml. of concentrated hydrochloric acid is added and the mixture boiled for three hours, cooled, washed with ethyl ether. The aqueous phase is made alkaline with sodium hydroxide solution, extracted with ether and the extracts dried over anhydrous magnesium sulfate. The solvent is evaporated to afford the title compound as a mixture of isomers.

Workup

  1. additionA mixture of 5.53 g
  2. temperatureat reflux under a nitrogen atmosphere
  3. customwhile removing water as it
  4. customforms in the reaction
  5. customreaches 195° C.
  6. temperaturethe mixture is cooled
  7. extractionextracted with ethyl acetate
  8. customThe extract is evaporated to dryness, 5 ml
  9. additionof concentrated hydrochloric acid is added
  10. temperaturecooled
  11. washwashed with ethyl ether
  12. extractionextracted with ether
  13. dry with materialthe extracts dried over anhydrous magnesium sulfate
  14. customThe solvent is evaporated

Sources & evidence

ORD record
ord-59ca9e55693a4b9da4d7c0b91113283b
Source dataset
uspto-grants-1982_01
Patent number
US04309545

Reaction notes

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