Methyl 2-(4-chloro-2-nitrophenyl)acetate → Methyl (4-chloro-2-[N-hydroxyamino] phenyl)acetate

HRID 374283ノート

反応式

HRID 374283 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])([O-])=[O:2].[PH2]([O-])=O.[Na+]>O1CCCC1.CS(C)=O.O.[Pd]>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:4]([NH:1][OH:2])[CH:9]=1

参加物

7

反応物 2

HCID 10944246Methyl 2-(4-chloro-2-nitrophenyl)acetateHCID 178527019HCID 178527019、化合物2 回

生成物 1

HCID 10954957Methyl (4-chloro-2-[N-hydroxyamino] phenyl)acetate収率 110.3%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl (2-nitro-4-chlorophenyl)acetate (5.0 g, 21.7 mmol) was dissolved in 250 ml of tetrahydrofuran and 15 ml of dimethyl sulfoxide. To this was added 900 mg of 10% Pd/C. A solution of 5.38 g of sodium hypophosphite in 18 ml of water was added dropwise over a 40 minute period. After stirring for 4 hours another 2.68 g of sodium hypophosphite (in 8 ml of water) was added over a 10 minute period. After stirring for one hour the reaction mixture was filtered through Celite and the filtrate diluted with 500 ml of CH2Cl2. The filtrate was washed with saturated aqueous NaHCO3 then brine and dried with Na2SO4. The solvents were evaporated under reduced pressure leaving 5.16 g of a yellow oil (110% of theory). NMR (300 MHz, CDCl3): 3.51 (2 H, s), 3.69 (3 H, s), 5.50 (1 H, br s), 6.88 (1 H, dd, J=1,8), 7.01 (1 H, d, J=8), 7.34 (1 H, d, J=1), 7.56 (1 H, br s).

後処理

  1. additionwas added over a 10 minute period
  2. filtrationwas filtered through Celite
  3. additionthe filtrate diluted with 500 ml of CH2Cl2
  4. washThe filtrate was washed with saturated aqueous NaHCO3
  5. dry with materialbrine and dried with Na2SO4
  6. customThe solvents were evaporated under reduced pressure

出典と根拠

ORDレコード
ord-f0610779bfc942a68ac197df9e39b9f1
出典データセット
uspto-grants-1992_11
特許番号
US05166401

反応ノート

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