1,2,3,4-Tetrahydroisoquinoline → 2-Acetyl-1,2,3,4-tetrahydroisoquinoline

HRID 1447110Notes

Reaction equation

HRID 1447110 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 7918Acetic Anhydride

Product 1

HCID 6002152-Acetyl-1,2,3,4-tetrahydroisoquinoline

Procedure

A mixture of 100 g. (0.75 mole) 1,2,3,4-tetrahydroisoquinoline and 150 ml. acetic anhydride was stirred at ambient temperature for 24 hours and then concentrated to dryness at reduced pressure. The residual liquid was dissolved in methylene chloride and solid potassium carbonate was added to neutralize the solution. The excess potassium carbonate was removed by filtration and the filtrate was concentrated to dryness at reduced pressure to afford 2-acetyl-1,2,3,4-tetrahydroisoquinoline as a yellow liquid.

Workup

  1. additionA mixture of 100 g
  2. concentrationconcentrated to dryness at reduced pressure
  3. dissolutionThe residual liquid was dissolved in methylene chloride
  4. additionsolid potassium carbonate was added
  5. customThe excess potassium carbonate was removed by filtration
  6. concentrationthe filtrate was concentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-c79b68032fbe4b7eb3ea1a3bcdf03850
Source dataset
uspto-grants-1982_02
Patent number
US04315935

Reaction notes

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