Ethyl bromoacetate → HCID 70048956, compound

HRID 862426Notes

Reaction equation

HRID 862426 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[ClH:28].O1CCOCC1>C(O)C>[ClH:28].[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinolineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 70048956HCID 70048956, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Nitro-1,2,3,4-tetrahydroisoquinoline (5.78 g) was dissolved in ethanol (400 ml), triethylamine (7.8 ml) and ethyl bromoacetate (4.5 g) were added, and the mixture was heated and refluxed for 1 hour. Most of the solvent was distilled off under reduced pressure, concentrated residue was extracted with ethyl acetate and the extracted solution was dried with anhydrous magnesium sulfate. The solvent distilled off under reduced pressure and the crude product obtained was purified by silica gel column chromatography using a solvent mixture, ethyl acetate:n-hexane=1:3, as a developer. The compound obtained was treated with a hydrochloric acid/dioxane solution to obtain ethyl 7-nitro-1,2,3,4-tetrahydro-isoquinoline-2-acetate hydrochloride (4.2 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1 hour
  3. distillationMost of the solvent was distilled off under reduced pressure, concentrated residue
  4. extractionwas extracted with ethyl acetate
  5. dry with materialthe extracted solution was dried with anhydrous magnesium sulfate
  6. distillationThe solvent distilled off under reduced pressure
  7. customthe crude product obtained
  8. customwas purified by silica gel column chromatography
  9. customThe compound obtained

Sources & evidence

ORD record
ord-a0f6c2a806f14b3887ff1701747dfae0
Source dataset
uspto-grants-1998_02
Patent number
US05719145

Reaction notes

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