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

HRID 1465138

Reaction equation

HRID 1465138 reaction equation
[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]

Participants

6

Reactant 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, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-6e8e0ecb24084ecb96e34e42ccf892d3
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Linked notes

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