Hydrochloric Acid → 4-oxo-5,6,7,8-tetrahydro-1H-cyclohepta[b]pyrrole-3-carboxylic acid

HRID 1290088노트

반응식

HRID 1290088 반응식
[O:1]=[C:2]1[C:11]2[C:10]([C:12]([O:14]CC)=[O:13])=[CH:9][NH:8][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl>[OH-].[Na+].C(O)C>[O:1]=[C:2]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][NH:8][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 18696565Ethyl 4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[B]pyrrole-3-carboxylate

생성물 1

HCID 223187424-oxo-5,6,7,8-tetrahydro-1H-cyclohepta[b]pyrrole-3-carboxylic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g,15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, and extracted 2X with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate then brine, dried over sodium sulfate, filtered through a small pad of Silica gel (5% methyl alcohol/dichloromethane), and the filtrate concentrated in vacuo to give ethyl 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylate (1.76 g). A solution of this ester in aqueous 5N sodium hydroxide (30 mL) and ethyl alcohol(6 mL) was heated at reflux for 1 hour, then cooled in an ice bath. The mixture was acidified with hydrochloric acid; the resulting precipitate was collected, rinsed with water followed by diethyl ether and allowed to dry to give 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid (1.17 g). m.p. 225°-227°C.

후처리

  1. temperatureat reflux for 1 hour
  2. temperaturecooled in an ice bath
  3. customthe resulting precipitate was collected
  4. washrinsed with water
  5. customto dry

출처 및 근거

ORD 기록
ord-d6f64b5f3d4f4caa8d9151e61eda8e0e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750702

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