5-Methyl-2-nitrobenzoic acid → Ethyl 2-(hydroxyimino)-2-(5-methyl-2-nitrobenzamido)acetate

HRID 383402

反応式

HRID 383402 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[OH:14][NH:15][C:16](=[NH:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(#N)C>[OH:14][N:15]=[C:16]([NH:22][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

参加物

6

反応物 4

HCID 183715-Methyl-2-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178472862HCID 178472862、化合物

生成物 1

HCID 136388713Ethyl 2-(hydroxyimino)-2-(5-methyl-2-nitrobenzamido)acetate収率 92.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To 5-methyl-2-nitro-benzoic acid (100 mg, 0.55 mmol), ethyl 2-(hydroxyamino)-2-imino-acetate (73 mg, 0.55 mmol), and HATU (210 mg, 0.55 mmol) were added acetonitrile (4 mL) and DIEA (96 μL, 0.55 mmol). The reaction was stirred at room temperature for 25 min resulting in a thick white precipitate. The solid was filtered, washed with water then dried to yield ethyl 2-(hydroxyimino)-2-(5-methyl-2-nitrobenzamido)acetate as a white solid (150 mg, 92% yield). LC/MS m/z 296.1 [M+H]+. 1H NMR (400.0 MHz, DMSO-do) δ 8.05 (d, J=8.3 Hz, 1H), 7.74 (d, J=0.9 Hz, 1H), 7.61 (d, J=8.4 Hz, 1H), 7.16 (br s, 2H), 4.28 (q, J=7.1 Hz, 2H), 2.47 (s, 3H), 1.28 (t, J=7.1 Hz, 3H).

後処理

  1. customresulting in a thick white precipitate
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customthen dried

出典と根拠

ORDレコード
ord-c0b6145d9eb140a4b930876ce69c9fd6
出典データセット
uspto-grants-2013_02
特許番号
US08367660B2

関連ノート

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