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

HRID 383402

반응식

HRID 383402 반응식
[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]

참가 물질

6

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c0b6145d9eb140a4b930876ce69c9fd6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367660B2

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