Dimethylformamide → HCID 58492458, compound

HRID 1874037Notes

Reaction equation

HRID 1874037 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:29](=[O:30])[C:28]3[C:19](=[C:20]([O:31][CH2:32][CH2:33][CH3:34])[CH:21]=[C:22]4[C:27]=3[O:26][CH2:25][CH2:24][CH2:23]4)[NH:18][CH:17]=2)=[CH:12][CH:11]=1.Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>C(OCC)(=O)C.O>[CH2:40]([O:39][C:37](=[O:38])[CH2:36][N:18]1[C:19]2[C:28](=[C:27]3[C:22](=[CH:21][C:20]=2[O:31][CH2:32][CH2:33][CH3:34])[CH2:23][CH2:24][CH2:25][O:26]3)[C:29](=[O:30])[C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:15][CH:14]=2)=[CH:17]1)[CH3:41]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 46224430HCID 46224430, compound

Product 1

HCID 58492458HCID 58492458, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil base, 80 mg, 2.0 mmol) was added to a DMF solution (10 ml) of 3-(4-methoxyphenyl)-10-propoxy-1,6,7,8-tetrahydro-5-oxa-1-aza-phenanthren-4-one (600 mg, 1.64 mmol), the resulting mixture was then stirred at room temperature for 5 minutes. Ethyl bromoacetate (330 mg, 2.0 mmol) was added thereto and the resulting mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a colorless oily substance ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate (700 mg, yield: 95%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. customfollowed by separation
  3. washThe thus-obtained organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5dcafa4ae6d42a1bd3030b419f4544a
Source dataset
uspto-grants-2012_11
Patent number
US08304546B2

Reaction notes

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