4-Bromophenylhydrazine hydrochloride → 3-Benzyl-5-bromo-2-methyl-1H-indole

HRID 731052Notes

Reaction equation

HRID 731052 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH2:11]([CH2:18][C:19](=O)[CH3:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[CH2:11]([C:18]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([Br:2])[CH:8]=2)[NH:9][C:19]=1[CH3:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 17355Benzyl acetone

Product 1

HCID 688163193-Benzyl-5-bromo-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The desired product was prepared using a procedure similar to step 1 of example 3. Thus, 4-bromophenylhydrazine, hydrochloride (4.694 g, 21 mmol) was reacted with benzylacetone (2.964 g, 20 mmol) in ethanol (60 ml) to give the product (3.199 g, 10.657 mmol, 51%) as a tan solid, mp 130-134° C. 1H NMR (DMSO-d6) δ 2.36 (s, 3H), 3.95 (s, 2H), 7.05 (dd, J=1.8, 8.4 Hz, 1H), 7.12 (t, J=7.2 Hz, 1H), 7.17-7.20 (m, 3H), 7.23 (t, J=7.8 Hz, 2H), 7.43 (d, J=1.7 Hz, 1H), 11.01 (s, 1H); [ESI(−)], m/z 298/300 (M−H)−.

Sources & evidence

ORD record
ord-a5fa4b4a27d145b4ad7aa5cf1ddde225
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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