Methyl bromoacetate → HCID 13280936, compound

HRID 1903632Notes

Reaction equation

HRID 1903632 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:7](=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C)C=O.O>[CH3:35][O:34][C:32](=[O:33])[CH2:31][N:19]1[C:20]([CH3:21])=[C:6]2[C:7]([CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=32)=[CH:18]1

Participants

6

Reactant 3

HCID 60984Methyl bromoacetateHCID 13067111HCID 13067111, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13280936HCID 13280936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In one portion, 2.0 g (5.8 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine were added to an ice-cooled solution of 0.8 g (7.1 mmol) of potassium t-butoxide in 30 ml of dry dimethylformamide. After stirring at 0° C. for 15 minutes, 0.65 ml (7.7 mmol) of methyl bromoacetate was added, and the resulting solution was stirred for 5 minutes. The mixture was diluted with water and extracted with ether. The ether solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to an oily residue. Purification of the residue by column chromatography (silica gel, 40 g; eluent, 5% ether in methylene chloride) gave after crystallization from a mixture of ether and petroleum ether 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester as off-white prisms, mp 174°-176° C.

Workup

  1. stirringthe resulting solution was stirred for 5 minutes
  2. extractionextracted with ether
  3. washThe ether solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to an oily residue
  6. customPurification of the residue by column chromatography (silica gel, 40 g; eluent, 5% ether in methylene chloride)
  7. customgave
  8. customafter crystallization
  9. additionfrom a mixture of ether and petroleum ether 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester as off-white prisms, mp 174°-176° C.

Sources & evidence

ORD record
ord-d7d8195b7f364789a0f6f62dfec0f105
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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