Sodium → CI 951

HRID 2248147Notes

Reaction equation

HRID 2248147 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[C:19]2[C:14](=[CH:15][CH:16]=[N:17][C:18]=2[O:31][CH:32]([CH3:34])[CH3:33])[NH:13][C:12]=1[CH3:35])=[O:10])[C:2]1C=CC=CC=1.[Na]>C(O)C>[CH2:1]([O:8][C:9]([C:11]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:28])[F:29])[C:19]2[C:14](=[CH:15][CH:16]=[N:17][C:18]=2[O:31][CH:32]([CH3:34])[CH3:33])[NH:13][C:12]=1[CH3:35])=[O:10])[CH3:2]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 13923228(+)-1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid benzyl ester

Product 1

HCID 128276CI 951

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.44 g (+)-1,4-dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid benzyl ester is introduced into a solution of 100 mg sodium in 90 mL anhydrous ethanol and boiled under reflux for 20 hours. The reaction mixture is evaporated, the residue is taken up in 50 mL dichloromethane and extracted three times with 20 mL amounts of water. The organic phase is dried over anhydrous sodium sulfate and thereafter evaporated to dryness. The residue is recrystallized from 20 mL n-hexane. The filter cake is dried to constant weight at 30° C. in a vacuum drying cabinet. Yield: 850 mg (67.38% of theory); mp 130° C.; [α]D =+110° C. (c=0.5/dichloromethane).

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe reaction mixture is evaporated
  3. extractionextracted three times with 20 mL amounts of water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe residue is recrystallized from 20 mL n-hexane
  7. customThe filter cake is dried to constant weight at 30° C. in a vacuum
  8. customdrying cabinet
  9. custom[α]D =+110° C. (c=0.5/dichloromethane)

Sources & evidence

ORD record
ord-151f346b6c974e61872df2caa7f24484
Source dataset
uspto-grants-1991_08
Patent number
US05037987

Reaction notes

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