Hydrochloric Acid → HCID 70392657, compound

HRID 1382905Notes

Reaction equation

HRID 1382905 reaction equation
[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[C:12](/[CH3:24])=[CH:13]/[C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)[NH:5][CH2:4][CH2:3]1.[CH2:26]=O.Cl>C(O)=O>[CH3:26][N:5]1[C:6]2[C:11](=[CH:10][C:9](/[C:12](/[CH3:24])=[CH:13]/[C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=3)=[CH:8][CH:7]=2)[C:2]([CH3:25])([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 70392883HCID 70392883, compound

Product 1

HCID 70392657HCID 70392657, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3.64 g of methyl 4-[(E)-2-(4,4-dimethyl-1,2,3,4-tetrahydro-6-quinolinyl)-2-methylvinyl]benzoate, 5 ml of 90% formic acid and 5 ml of 40% aqueous formaldehyde is heated at 95° C. for 12 hours. The reaction medium is then cooled and 1.5 ml of concentrated hydrochloric acid is added. The formic acid and excess formaldehyde are removed by evaporation in vacuo. The resulting mixture is then made strongly basic and extracted with dichloromethane. The dichloromethane extracts are combined, dried (MgSO4) and evaporated in vacuo to give the title compound.

Workup

  1. temperatureThe reaction medium is then cooled
  2. customThe formic acid and excess formaldehyde are removed by evaporation in vacuo
  3. extractionextracted with dichloromethane
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5378bfbbdfd446de86893f047bd32795
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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