HCID 12881937, compound → 11,12-Dihydro-4-methoxydibenz(b,f)(1,4)oxazepine-8-carboxylate

HRID 1577985Notes

Reaction equation

HRID 1577985 reaction equation
[CH:1]([C:3]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:4]=1[O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-])=O)=O>O1CCOCC1.C(O)C.[Ni]>[CH3:25][O:24][C:20]1[C:4]2[O:5][C:6]3[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=3[NH:17][CH2:1][C:3]=2[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 1

HCID 12881937HCID 12881937, compound

Product 1

HCID 33923711,12-Dihydro-4-methoxydibenz(b,f)(1,4)oxazepine-8-carboxylateYield 77%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 4-(2-formyl-6-methoxyphenoxy)-3-nitrobenzoate (145 g) in dioxane (1.2 l) and ethanol (150 ml) was hydrogenated over Raney nickel catalyst (60 ml) at room temperature under atmospheric pressure. After a pre-calculated amount of hydrogen was absorbed, the catalyst was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was treated with ethanol (20 ml) to crystallize and then the separated crystals were collected by filtration. Recrystallization from ethanol gave ethyl 10,11-dihydro-4-methoxydibenz[b,f][1,4]oxazepine-8-caboxylate (96 g) as colorless needles. (Yield: 77%, m.p. 121°-122° C.)

Workup

  1. customAfter a pre-calculated amount of hydrogen was absorbed
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. additionThe residue was treated with ethanol (20 ml)
  5. customto crystallize
  6. filtrationthe separated crystals were collected by filtration
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-5b7da9b2a81a4b3c97052baa8800d72c
Source dataset
uspto-grants-1981_09
Patent number
US04290953

Reaction notes

Loading…