Formaldehyde → HCID 70608718, compound

HRID 426761Notes

Reaction equation

HRID 426761 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH:7]3[CH:11]([CH:12]([C:13]4[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=4)[C:4]=2[CH:3]=1)[CH2:10][NH:9][CH2:8]3.[CH2:22]=O>C(O)=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH:7]3[CH:11]([CH:12]([C:13]4[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=4)[C:4]=2[CH:3]=1)[CH2:10][N:9]([CH3:22])[CH2:8]3

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 70608335HCID 70608335, compound

Product 1

HCID 70608718HCID 70608718, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1.5 g of (3aRS,4SR,9aSR)-6-chloro-4-(p-chlorophenyl)-3a,4,9,9a-tetrahydro-benz[f]isoindoline, 10 cc of 100% formic acid and 10 cc of a 40% aqueous formaldehyde solution is heated to the boil at reflux for 2 hours in an atmosphere of nitrogen. The mixture is concentrated by evaporation, the residue is taken up in water, the solution is made alkaline with concentrated caustic soda solution and is extracted with methylene chloride. Ether is added to the dried extracts until they are turbid, filtration through Hyflo and concentration by evaporation are effected, whereby the title compound is obtained as residue. M.P. 133°-135° (after crystallization from ether).

Workup

  1. temperatureis heated to the boil
  2. temperatureat reflux for 2 hours in an atmosphere of nitrogen
  3. concentrationThe mixture is concentrated by evaporation
  4. extractionis extracted with methylene chloride
  5. additionEther is added to the dried extracts until they
  6. filtrationturbid, filtration
  7. concentrationthrough Hyflo and concentration
  8. customby evaporation

Sources & evidence

ORD record
ord-2921870ef83948f49562bee012d8c7d6
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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