Acetyl chloride → 2'-Acetylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

HRID 1758523Notes

Reaction equation

HRID 1758523 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:3][NH:2]1.C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([N:2]1[CH2:3][C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

Product 1

HCID 159174522'-Acetylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]Yield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (8.0 g) and triethylamine 4.1 g) in dichloromethane (35 ml) is added dropwise acetyl chloride (3.2 g) in dichloromethane (20 ml). After stirring at ambient temperature for 20 hours, the reaction mixture is washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent yields a solid (6.2 g), of which 2.5 g is recrystallized from ethyl acetate to yield 1.4 g (56%) of product as a powder, mp 141°-142°.

Workup

  1. washthe reaction mixture is washed with water (2x), saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-e8572dd4646e4bc6b0815b57b036f374
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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