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Sulfamic Acid → Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

HRID 570381
ノート
印刷プレビュー

反応式

HRID 570381 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.NS(O)(=O)=O.[C:24]([O:30][CH3:31])(=[O:29])[CH2:25][C:26]([CH3:28])=O>CCOC(C)=O>[CH3:28][C:26]1[C:25]([C:24]([O:30][CH3:31])=[O:29])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:1]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5987Sulfamic AcidHCID 7757Methyl acetoacetateHCID 156812-Amino-5-nitrobenzophenone

生成物 1

HCID 26609017Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate収率 80%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-amino-5-nitrobenzophenone (1 g, 4.1 mmol), H2NSO3H (0.04 g, 041 mmol) and methyl acetoacetate (1.11 ml, 10.3 mmol) was stirred overnight at 120° C. under N2, than cooled to room temperature, diluted to 100 ml with EtOAc and washed with H2O. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by crystallization from EtOH to give pure product as a creamy solid (1.05 g, 80%). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=2.5 Hz, 1H), 8.48 (dd, J=2.5, 9.2 Hz, 1H), 7.53(m, 3H), 7.34(m, 2H), 3.59(s, 3H), 2.8(s, 3H).

後処理

  1. temperaturethan cooled to room temperature
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customfiltrate evaporated to dryness under reduced pressure
  6. customThe residue was purified by crystallization from EtOH

出典と根拠

ORDレコード
ord-2057103ac4fa44a582aa7092f6b7487c
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09023848B2

反応ノート

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