Formic Acid → HCID 20283263, compound

HRID 463351Notes

Reaction equation

HRID 463351 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][NH:6]1)[CH3:3].[CH:21](O)=[O:22]>C1(C)C=CC=CC=1>[CH:21]([N:6]1[CH2:7][CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]1[CH2:4][N:2]([CH3:1])[CH3:3])=[O:22]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13457439HCID 13457439, compound

Product 1

HCID 20283263HCID 20283263, compoundYield 120%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-1-dimethylaminomethyl-4-phenylisoquinoline base (Example 2) (9.5 g, 0.035 m) in toluene (100 ml) under nitrogen was added formic acid (8.05 g, 0.175 m) and the mixture heated to reflux in a Dean and Stark apparatus. After 3 ml of water were collected, the mixture was cooled, treated with 250 ml of 5% NaOH, and extracted with ether (1×150 ml) and then chloroform (3×100 ml) and the combined organic extracts dried over MgSO4. Evaporation of the solvents gave 12.6 g of 1,2,3,4-tetrahydro-2-formyl-1-dimethylaminomethyl-4-phenylisoquinoline as a yellow oil. This material was used directly for additional chemical processing without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux in a Dean and Stark apparatus
  3. customAfter 3 ml of water were collected
  4. temperaturethe mixture was cooled
  5. additiontreated with 250 ml of 5% NaOH
  6. extractionextracted with ether (1×150 ml)
  7. dry with materialchloroform (3×100 ml) and the combined organic extracts dried over MgSO4
  8. customEvaporation of the solvents

Sources & evidence

ORD record
ord-bf9ac13153584762b0ffaa0dda5341a3
Source dataset
uspto-grants-1985_05
Patent number
US04518779

Reaction notes

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