Water → HCID 19074340, compound

HRID 964935Notes

Reaction equation

HRID 964935 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:23]=[CH:22][C:11]2[C:12](=O)[NH:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[O:16][C:10]=2[CH:9]=1.O>O1CCCC1.O1CCOCC1>[Cl:7][C:8]1[CH:23]=[CH:22][C:11]2[CH2:12][NH:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[O:16][C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 190743493158-88-1HCID 21226445Aluminium lithium hydride

Product 1

HCID 19074340HCID 19074340, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

LiAlH4 (1M) in tetrahydrofuran (100 ml) was added dropwise to a mixture of 3-chlorodibenz[b,f][1,4]oxazepin-11(10H)-one (12.3 g) (prepared as described in Indian J. Chem. 1974, 12(3), 227-35) in 1,4-dioxane (400ml) under a N2 atmosphere. The mixture was stirred, refluxed for 1 hour 30 minutes, cooled and water was added dropwise. The mixture was acidified and extracted with EtOAc. The organic layer was dried with Na2SO4, filtered off and evaporated. The residue was purified by open column chromatography over silica gel (eluent: CH2Cl2). The pure fractions were collected and evaporated, yielding 9.74 g (84%) of 3-chloro-10,11-dihydrodibenz[b,f]-[1,4]oxazepine (interm.8).

Workup

  1. temperaturerefluxed for 1 hour 30 minutes
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered off
  6. customevaporated
  7. customThe residue was purified by open column chromatography over silica gel (eluent: CH2Cl2)
  8. customThe pure fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-ac3ae8b737ee474e9feeec00caf212b9
Source dataset
uspto-grants-1998_06
Patent number
US05773433

Reaction notes

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