Hydrochloric Acid → Spiro[cyclobutane-1,3'-indolin]-2'-one

HRID 74519

反応式

HRID 74519 の反応式
[C:1]1([N:7]([C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[O:10])N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Ca+2].[H-].[H][H].Cl.[OH-].[Na+]>CO.O>[NH:7]1[C:1]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]2([CH2:14][CH2:13][CH2:12]2)[C:9]1=[O:10]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3033859Calcium hydrideHCID 67337909N-phenylcyclobutanecarbohydrazideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 13728292Spiro[cyclobutane-1,3'-indolin]-2'-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
230 °C

実験手順

Under a nitrogen atmosphere 1.50 g (7.89 mmol) cyclobutanecarboxylic acid N-phenylhydrazide and 530 mg (12.6 mmol) calcium hydride were mixed thoroughly and heated to 230° C. The mixture was stirred for 30 min at 230° C. and then cooled to RT again. The reaction mixture was carefully mixed with a solution of 7 mL water and 16 mL methanol. It was stirred for 1 h until no more hydrogen was released. Then the pH was adjusted to 1 with concentrated hydrochloric acid solution and the mixture was stirred for 1 h at 100° C. Using 4M sodium hydroxide solution the pH was adjusted to 3 and stirred overnight at RT. The precipitated substance was suction filtered and washed with 10 mL water. The mother liquor was evaporated down i.vac. and the residue was purified by preparative HPLC. The product fractions were combined, evaporated down i.vac. and dried.

後処理

  1. temperaturecooled to RT again
  2. stirringthe mixture was stirred for 1 h at 100° C
  3. stirringstirred overnight at RT
  4. filtrationfiltered
  5. washwashed with 10 mL water
  6. customThe mother liquor was evaporated down i.vac
  7. customand the residue was purified by preparative HPLC
  8. customevaporated down i.vac
  9. customand dried

出典と根拠

ORDレコード
ord-7187c3dd5c874e0b9deb3e1aba52ef82
出典データセット
uspto-grants-2014_09
特許番号
US08829006B2

関連ノート

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