Benzyl Bromide → Benzyl 1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

HRID 1596535Notes

Reaction equation

HRID 1596535 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[CH:8]=[C:7]1[C:16]([OH:18])=[O:17].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[CH:8]=[C:7]1[C:16]([O:18][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:17]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 9905846HCID 9905846, compound

Product 1

HCID 9910428Benzyl 1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3,4-Dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylic acid (1.32 g) and benzyl bromide (0.68 g) was stirred in DMF (10 mL) over potassium carbonate (0.48 g) for 18 hours. The DMF was removed in vacuo and the residue was dissolved in ethyl acetate (50 mL). The organic solution was washed with 2M HCl and dried over MgSO4. The solvents were removed in vacuo to afford the title compound as a pale solid (1.63 g, 97%), NMR d(CDCl3) 2.20 (2H, di), 2.50 (2H, t), 2.70 (2H, t), 5.21 (2H, m), 5.55 (2H, s), 6.80 (1H, d), 7.10 (1H,s), 7.35(6H, s), 7.50(1H, s); M/z(+)430, 428 (M+).

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe organic solution was washed with 2M HCl
  4. dry with materialdried over MgSO4
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-4c285953599f442a826a482dc0a6a6ed
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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