Phosphorus oxychloride → 4-Chloro-6-(3,4-dimethoxy-phenyl)-[1,5]naphthyridine-3-carboxylic acid ethyl ester

HRID 445786

Reaction equation

HRID 445786 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[N:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[CH:11][CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:29]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:29])=[N:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469508HCID 178469508, compound

Product 1

HCID 596197304-Chloro-6-(3,4-dimethoxy-phenyl)-[1,5]naphthyridine-3-carboxylic acid ethyl ester

Conditions

Temperature
125 °C

Procedure

A mixture of 6-(3,4-dimethoxy-phenyl)-4-hydroxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (Stage 249.1.3, 493 mg, 1.391 mmol) in POCl3 was stirred at 125° C. for 1.5 h. Then the RM was evaporated to dryness. The residue was quenched with saturated aqueous NaHCO3. The suspension was filtered, the cake was washed with water and dried in the vacuum oven to give the title compound as a brown solid. Used for next step without further purification. (HPLC: tR 3.80 min (Method A); M+H=373 MS-ES)

Workup

  1. customThen the RM was evaporated to dryness
  2. customThe residue was quenched with saturated aqueous NaHCO3
  3. filtrationThe suspension was filtered
  4. washthe cake was washed with water
  5. customdried in the vacuum oven

Sources & evidence

ORD record
ord-bf5767b4751b4bd2a0dcaa0785eb9279
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Linked notes

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