Acetyl bromide → HCID 20531692, compound

HRID 1759321Notes

Reaction equation

HRID 1759321 reaction equation
Br.[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:20])[CH:14]=1)[N:10]([CH3:21])[CH2:9][CH2:8]2.[C:22]([Br:25])(=[O:24])[CH3:23]>FC(F)(F)C(O)=O>[BrH:25].[C:22]([O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:3](=[O:2])[CH3:12])=[C:15]([O:20][C:16](=[O:19])[CH3:15])[CH:14]=1)[N:10]([CH3:21])[CH2:9][CH2:8]2)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 20531683HCID 20531683, compound

Product 1

HCID 20531692HCID 20531692, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1.0 g of 8-hydroxy-1-(3,4-dihydroxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide prepared as in Example 4 above and 200 ml of trifluoroacetic acid is mixed with 1.3 ml of acetyl bromide. After heating at reflux for 2 hours, the mixture is evaporated to dryness. The residue is purified by recrystallization to give 8-acetoxy-1-(3,4-diacetoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide. Similarly isobutyryloxy, propionyloxy, isovaleryloxy, n-butylryloxy and n-heptanoyloxy derivatives are prepared.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hours
  3. customthe mixture is evaporated to dryness
  4. customThe residue is purified by recrystallization

Sources & evidence

ORD record
ord-6f494e64ba7a48d7804e9937f1de5768
Source dataset
uspto-grants-1982_07
Patent number
US04340600

Reaction notes

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