Chloroacetyl chloride → HCID 22857195, compound

HRID 129230Notes

Reaction equation

HRID 129230 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:17][C:8]2=[CH:9][NH:10][C:11]3[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([C:7]=32)[C:5]1([OH:19])[CH3:18])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:27][C:28](Cl)=[O:29]>C(OCC)(=O)C>[CH2:1]([N:3]1[C@@H:4]2[CH2:17][C:8]3[C:7]4[C:11]([NH:10][CH:9]=3)=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:6]=4[C@@:5]2([CH3:18])[O:19][CH2:27][C:28]1=[O:29])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 19372773HCID 19372773, compound

Product 1

HCID 22857195HCID 22857195, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-dihydro-4-ethylamino-5-hydroxy-6-methoxy-5-methyl-5H-benz[cd]indole (646 mg 2.48 mmol) in ethyl acetate (25 ml) was added a saturated aqueous solution of sodium carbonate (24 ml). To the mixture was added, while stirring vigorously, chloroacetyl chloride (1.2 equivalent). After completion of the reaction, the organic layer was separated and washed with an aqueous saline solution, followed by drying (anhydrous Na2SO4). The solvent was distilled off under reduced pressure. The residue was cyclized and, then, purified by means of silica gel column chromatography (eluting with n-hexane-ethyl acetate (2:7)) to afford 517 mg (72%) of the title compound as an amorphous crystalline product.

Workup

  1. additionTo the mixture was added
  2. customAfter completion of the reaction
  3. customthe organic layer was separated
  4. washwashed with an aqueous saline solution
  5. dry with materialby drying (anhydrous Na2SO4)
  6. distillationThe solvent was distilled off under reduced pressure
  7. custompurified by means of silica gel column chromatography (eluting with n-hexane-ethyl acetate (2:7))

Sources & evidence

ORD record
ord-6d3b3c55d57b4212bd277c06be521659
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

Loading…