Pyridine → HCID 772645, compound

HRID 1247045Notes

Reaction equation

HRID 1247045 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[C:18]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[O:27])=[CH:29][CH:30]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8635Methyl AnthranilateHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 772645HCID 772645, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of methyl 2-aminobenzoate (5 g, 33.1 mmol) and pyridine (5.3 g, 66 mmol) in dichloromethane (100 mL) was added 4-dimethylaminopyridine (0.2 g, 1.6 mmol). The mixture was cooled to 0° C. and treated with 4-tert-butylbenzoyl chloride (6.5 g, 33.1 mmol). After stirring overnight, the reaction mixture was diluted with dichloromethane (100 mL) and washed twice with 1 M aqueous citric acid (100 mL). The organic layer was then washed sequentially with water (100 mL) and 5 N aqueous HCl. It was dried over MgSO4, filtered and concentrated in vacuo to give 10.68 g (quantitative) of a colorless oil.

Workup

  1. washwashed twice with 1 M aqueous citric acid (100 mL)
  2. washThe organic layer was then washed sequentially with water (100 mL) and 5 N aqueous HCl
  3. dry with materialIt was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 10.68 g (quantitative) of a colorless oil

Sources & evidence

ORD record
ord-592e11872cfa4b64b987b96c055b1a9c
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

Loading…