Ammonium Chloride → Methyl 7-amino-2,3-dihydro-1,4-benzodioxin-6-carboxylate

HRID 1595774노트

반응식

HRID 1595774 반응식
[CH3:1][O:2][C:3]([C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1)=[O:4].[NH4+].[Cl-]>CO.O.[Fe]>[CH3:1][O:2][C:3]([C:5]1[C:14]([NH2:15])=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1)=[O:4]

참가 물질

6

반응물 2

HCID 25517Ammonium Chloride3회HCID 10537941Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

생성물 1

HCID 3146109Methyl 7-amino-2,3-dihydro-1,4-benzodioxin-6-carboxylate수율 90.5%

시약·촉매·용매 3

HCID 23925Iron촉매3회HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of 12.0 g (50.2 mmol) of 7-nitro-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester, 11.2 g (201 mmol) of powdered Fe and 13.3 g (257 mmol) of NH4Cl in 175 ml of MeOH and 70 mL of H2O was refluxed for 5.5 h. An additional 11.2 g of Fe and 13.3 g of NH4Cl was added and the mixture was heated for 5.5 h more. Finally, 5.5 g of Fe and 6.5 g of NH4Cl was added and the mixture was heated for 4 h. The cooled reaction was filtered through Celite, the pad was washed well with MeOH and the filtrate and washings were combined. The solvent was removed and the residue was slurried in H2O and collected. The crude product was filtered through silica (CHCl3) to give 9.5 g of the title compound as tan crystals: mass spectrum (electrospray, m/e): M+H 209.9.

후처리

  1. temperaturewas refluxed for 5.5 h
  2. temperaturethe mixture was heated for 5.5 h more
  3. temperaturethe mixture was heated for 4 h
  4. customThe cooled reaction
  5. filtrationwas filtered through Celite
  6. washthe pad was washed well with MeOH
  7. customThe solvent was removed
  8. customcollected
  9. filtrationThe crude product was filtered through silica (CHCl3)

출처 및 근거

ORD 기록
ord-39f8ae95eb1a4941a9cbe6b8d592ceb0
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288082B1

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