Acetyl bromide → HCID 12833523, compound

HRID 2058996Notes

Reaction equation

HRID 2058996 reaction equation
Br.[Cl:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:7]=2[CH:6]=[C:5]([OH:21])[C:4]=1[OH:22].[C:23]([Br:26])(=[O:25])[CH3:24]>FC(F)(F)C(O)=O>[BrH:26].[Cl:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:23](=[O:25])[CH3:24])=[CH:18][CH:19]=3)[C:7]=2[CH:6]=[C:5]([O:21][C:17](=[O:20])[CH3:16])[C:4]=1[O:22][C:5](=[O:21])[CH3:4]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 11957552Fenoldopam monohydrobromide

Product 1

HCID 12833523HCID 12833523, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-Chloro-7,8-dihydroxy-1-p-hydroxyphenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (Example 2, 1.0 g) was slurried in 200 ml of trifluoroacetic acid then 1.29 ml of acetyl bromide was added. The mixture was heated at reflux for 2 hours then stirred for 2 hours. After evaporation to dryness the residue was taken up in benzene and concentrated to give a solid which was recrystallized from ethylacetatehexane to give 6-chloro-7,8-diacetoxy-1-(p-acetoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide; m.p. 214.5°-217°, 0.77 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customAfter evaporation to dryness the residue
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas recrystallized from ethylacetatehexane

Sources & evidence

ORD record
ord-93e01013a1a94587a9d8702adc8f09b9
Source dataset
uspto-grants-1982_03
Patent number
US04321195

Reaction notes

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