Methyl 3,3-dimethoxypropionate → HCID 22917747, compound

HRID 2379708Notes

Reaction equation

HRID 2379708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:18][O:19][CH:20]([O:26][CH3:27])[CH2:21][C:22](OC)=[O:23].C[O-].[Na+].[Na]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10]3[C:11](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:21]([CH:20]([O:26][CH3:27])[O:19][CH3:18])[C:22]2=[O:23])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 81924Methyl 3,3-dimethoxypropionateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 53987074HCID 53987074, compound

Product 1

HCID 22917747HCID 22917747, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 42.7 g of 2-(3,5-dichlorophenyl)aminonicotinaldehyde, prepared in Example 29, in 500 ml of tetrahydrofuran containing 35.6 g of methyl 3,3-dimethoxypropionate, and a solution of sodium methylate prepared from 5.5 g of sodium in 100 ml of methanol, are stirred for 24 h at room temperature. The reaction mixture is subsequently concentrated under vacuum, water is then added and the crystals formed are filtered off, washed carefully with water and dried to give 44.25 g of 1-(3,5-dichlorophenyl)-1,2-dihydro-3-dimethoxymethyl-2-oxo-1,8-naphthyridine in the form of white crystals melting at 190° C. Yield 75.7%.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated under vacuum, water
  2. additionis then added
  3. customthe crystals formed
  4. filtrationare filtered off
  5. washwashed carefully with water
  6. customdried

Sources & evidence

ORD record
ord-c47b63f22d9547e6a02da8433d870a95
Source dataset
uspto-grants-1994_11
Patent number
US05364860

Reaction notes

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