Thionyl Chloride → 1-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carbonyl chloride

HRID 2299113Notes

Reaction equation

HRID 2299113 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:15]=[C:14]([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([OH:28])=O)=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[C:13]2[CH2:12][CH:11]=[CH:10][CH2:9][C:8]=2[N:7]=1>C(Cl)Cl>[CH3:5][C:6]1[CH:15]=[C:14]([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([Cl:3])=[O:28])=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[C:13]2[CH2:12][CH:11]=[CH:10][CH2:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 222586981-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carboxylic acid

Product 1

HCID 222583801-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carbonyl chlorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (5 ml) was added to a suspension of the 1-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carboxylic acid from step (402a) (0.67 g, 2.1 mmol) in methylene chloride (15 ml) and was heated to reflux for 2 hs. The reaction was cooled to room temperature, concentrated in vacuo to give the 1-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carbonyl chloride (0.68 g, 80%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hs
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a6f2e66015a497fac5aa14e3072c238
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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