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

HRID 648098Notes

Reaction equation

HRID 648098 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-704b64a44c6e49a4ad2dbf714a39a0bd
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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