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

HRID 383402

Reaktionsgleichung

Reaktionsgleichung von HRID 383402
[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]

Komponenten

6

Edukt 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, Verbindung

Produkt 1

HCID 136388713Ethyl 2-(hydroxyimino)-2-(5-methyl-2-nitrobenzamido)acetateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c0b6145d9eb140a4b930876ce69c9fd6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367660B2

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