1-Phenyl-cyclopropanecarbonyl chloride → HCID 67160441、化合物

HRID 469659

反応式

HRID 469659 の反応式
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Zn+])=[O:6])[CH3:3].[C:14]1([C:20]2([C:23](Cl)=[O:24])[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([C:20]2([C:23]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:5]([O:4][CH2:2][CH3:3])=[O:6])=[O:24])[CH2:21][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 2

HCID 27603721-Phenyl-cyclopropanecarbonyl chlorideHCID 178468809HCID 178468809、化合物

生成物 1

HCID 67160441HCID 67160441、化合物収率 66.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (2-(ethoxycarbonyl)phenyl)zinc(II) bromide (2.2 mL, 1.1 mmol) was added to a mixture of 1-phenylcyclopropanecarbonyl chloride (0.200 g, 1.1 mmol) and Pd(PPh3)4 (0.0644 g, 0.056 mmol) in THF (1.1 mL), stirred for 2 hours, diluted with EtOAc, washed with 1N HCl and brine, dried (Na2SO4), filtered, and chromatographed (20% Et2O/hexanes) to give 216.2 mg of impure ethyl 2-(1-phenylcyclopropanecarbonyl)benzoate. A mixture of impure ethyl 2-(1-phenylcyclopropanecarbonyl)benzoate (0.216 g, 0.735 mmol) and hydrazine hydrate (0.13 mL, 2.298 mmol) in ethanol (3 mL) was stirred at 75° C. overnight, and concentrated to give 179.7 mg of impure 4-(1-phenylcyclopropyl)phthalazin-1(2H)-one, which was treated with O-(diphenylphosphoryl)hydroxylamine using a method similar to that described in Example 1B to give impure 2-amino-4-(1-phenylcyclopropyl)phthalazin-1(2H)-one.

後処理

  1. washwashed with 1N HCl and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed (20% Et2O/hexanes)

出典と根拠

ORDレコード
ord-51fe9010a703484588447859c86aee1b
出典データセット
uspto-grants-2014_01
特許番号
US08629143B2

関連ノート

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