Pyridine → HCID 22046696, compound

HRID 1830962Notes

Reaction equation

HRID 1830962 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[C:19](Cl)([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>ClCCl>[CH3:12][O:11][C:10]1[C:2]([NH:1][C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 22046696HCID 22046696, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-amino-3-methoxybenzoic acid 97 (1 g, 6.0 mmol) and pyridine (0.97 mL, 12.0 mmol) were dissolved in dry dichloromethane (30 mL). The resulting mixture was cooled and Troc-Cl (0.9 mL, 6.6 mmol) was added drop wise. The reaction mixture was allowed to stir overnight at room temperature, then washed with HCl (1N, 50 mL), water (50 mL) and brine (50 mL). The organic phase was dried over MgSO4 and evaporated to yield 1.42 g of crude product, which was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was cooled
  2. washwashed with HCl (1N, 50 mL), water (50 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-510cb86c7766437c8f63dd45cc852060
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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