Ammonium Chloride → HCID 18319638, compound

HRID 1699400Notes

Reaction equation

HRID 1699400 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:19]([O-])=O)[C:7]2[O:13][CH2:12][CH2:11][C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=2[CH:18]=1>CO.O.[Fe]>[Cl:3][C:4]1[CH:5]=[C:6]([NH2:19])[C:7]2[O:13][CH2:12][CH2:11][C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=2[CH:18]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18319578HCID 18319578, compound

Product 1

HCID 18319638HCID 18319638, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of iron (reduced, 13.6 g) and ammonium chloride (1.6 g) in a mixture of methanol (140 ml) and water (50 ml) was added methyl 2,3-dihydro-7-chloro-9-nitro-1-benzoxepin-4-carboxylate (13.8 g) in portions under reflux. The reaction mixture was stirred for 6 hours under reflux. The iron powder was filtered off and the solvent was removed by concentration. The residue was diluted with ethyl acetate. The organic solvent was washed successively with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel using chloroform as an eluent. The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 2,3-dihydro-7-chloro-9-amino-1-benzoxepin-4-carboxylate (6.8 g).

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux
  3. filtrationThe iron powder was filtered off
  4. customthe solvent was removed by concentration
  5. additionThe residue was diluted with ethyl acetate
  6. washThe organic solvent was washed successively with saturated aqueous sodium bicarbonate and water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel
  10. additionThe eluted fractions containing the desired product
  11. customwere collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb6d9c38e89945f699a2ab9e97439fa6
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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