Acetic Acid → HCID 54269470, compound

HRID 904194Notes

Reaction equation

HRID 904194 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:17][C:3]1=2.[H-].[Na+].O.C(O)(=O)C.[CH3:30][C:31]1([CH3:38])[O:35][CH:34](CO)[CH2:33][O:32]1>>[CH3:30][C:31]1([CH3:38])[O:35][CH2:34][CH:33]([CH2:22][O:21][C:19](=[O:20])[CH2:18][C:15]2[CH:16]=[CH:17][C:3]3[N:2]([CH3:1])[CH2:8][C:7]4[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=4[C:5](=[O:13])[C:4]=3[CH:14]=2)[O:32]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 7528SolketalHCID 24758Sodium hydrideHCID 23333585HCID 23333585, compound

Product 1

HCID 54269470HCID 54269470, compound

Procedure

Methyl 5,6-dihydro-5-methyl-11-oxodibenz[b,e]azepine-2-acetate (1.5 g) was dissolved in Solketal (20 ml), and 50% oily sodium hydride (0.2 g) was added. The mixture was maintained at 80°-100° C. under reduced pressure using an aspirator. The reaction mixture was poured into water (150 ml) and acetic acid (0.5 ml), and the system was extracted with dichloromethane. The extract was dried over MgSO4, and then, the solvent was distilled off. The residual oily matter was subjected to liquid column chromatography using 100 g of Wakogel C-200 to afford the desired compound as a yellow oily material (0.950 g) eluted with a mixed liquid of benzene-dichloromethane (1:1).

Workup

  1. temperatureThe mixture was maintained at 80°-100° C. under reduced pressure
  2. extractionthe system was extracted with dichloromethane
  3. dry with materialThe extract was dried over MgSO4
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-1e8ac28f084b411dbae1c5370254c380
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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