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

HRID 1290088

反応式

HRID 1290088 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6f64b5f3d4f4caa8d9151e61eda8e0e
出典データセット
uspto-grants-1998_05
特許番号
US05750702

関連ノート

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