Pyridine → HCID 22046664, compound

HRID 1830964Notes

Reaction equation

HRID 1830964 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]([Cl:8])([Cl:7])[Cl:6])=[O:2].[NH2:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].N1C=CC=CC=1>ClCCl>[CH3:21][O:20][C:18]1[C:17]([O:22][CH3:23])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([NH:10][C:1]([O:3][CH2:4][C:5]([Cl:8])([Cl:7])[Cl:6])=[O:2])[CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 797364,5-Dimethoxyanthranilic acidHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 22046664HCID 22046664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Troc-Cl (0.76 ml, 5.56 mmol) in dry dichloromethane (10 mL) was added dropwise to 2-amino-4,5-dimethoxybenzoic acid 102 (1 g, 5.1 mmol) and pyridine (0.82 ml, 10.1 mmol) in dry dichloromethane (20 ml) at 0° C. The reaction mixture was allowed to stir overnight at room temperature and then washed with dilute HCl (1N, 2×25 ml), water (2×25 ml) and brine (20 ml). The organic phase was dried over MgSO4 and evaporated to yield of crude product (1.6 g), which was used in the next step without further purification.

Workup

  1. washwashed with dilute HCl (1N, 2×25 ml), water (2×25 ml) and brine (20 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated to yield of crude product (1.6 g), which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2b9355a724214e0884c708e1f2c16a4e
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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