Benzyl Bromide → HCID 18972163, compound

HRID 2395360Notes

Reaction equation

HRID 2395360 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][C:3]([C:4]=23)=[C:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][C:3]([C:4]=23)=[C:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18972171HCID 18972171, compound

Product 1

HCID 18972163HCID 18972163, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 1,3,4,5-tetrahydro-benz[cd]indole-2-carboxylate (0.40 g, 1.74 mmol) was added to a suspension of 60% sodium hydride (0.077 g, 1.92 mmol) in N,N-dimethylformamide (5 ml), followed by stirring at room temperature for 30 minutes. Then, benzyl bromide (0.36 g, 2.09 mmol) was added and the resulting mixture was stirred for 1.5 hours. Thereafter, the same after-treatment as in Reference Example 1 was carried out to obtain an oil of ethyl 1,3,4,5-tetrahydro -1benzyl-benz[cd]indole-2-carboxylate. 1 Hnmr (CDC13) δ:

Workup

  1. stirringthe resulting mixture was stirred for 1.5 hours

Sources & evidence

ORD record
ord-83832b6cfb4c48f1a6757c1dd0ae9712
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

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