Acetyl chloride → HCID 131722281, compound

HRID 279008Notes

Reaction equation

HRID 279008 reaction equation
C([Cl:4])(=O)C.[OH:5][N:6]1[C:15](=[O:16])[C:14]2[CH:17]=[C:18]([O:27][CH3:28])[C:19]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7]1=[O:29]>C(O)C>[ClH:4].[OH:5][N:6]1[C:15](=[O:16])[C:14]2[CH:17]=[C:18]([O:27][CH3:28])[C:19]([N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7]1=[O:29]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 22623915HCID 22623915, compound

Product 1

HCID 131722281HCID 131722281, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Benzyloxy-6-bromo-5-methoxy-benzo[de]isoquinoline-1,3-dione (0.5 g, from Example Z) was reacted with N-methylpiperazine (30 mL) following the procedure of Example 18 to give 0.5 g of 2-benzyloxy-5-methoxy-6-(4-methyl-piperazin-1-yl)-benzo[de]isoquinoline-1,3-dione. Hydrogenation of 2-benzyloxy-5-methoxy-6-(4-methyl-piperazin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.3 g) at 40 psi in the presence of Pd/C (10%) in DMA (20 mL) afforded 0.2 g of the title compound as the free base. A solution of acetyl chloride (0.03 mL) in ethanol (1 mL) was added to a solution of 2-hydroxy-5-methoxy-6-(4-methyl-piperazin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.12 g, 0.4 mmol) in ethanol (5 mL). The solution was stirred for 30 minutes, and the precipitate was filtered, washed with ether, and dried to give 0.13 g of the title compound as the HCl salt, mp 296-300° C.;

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-e36d3fd54904459dbabd8e28d36aa926
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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