Methylamine → N-methyl-3-(methylamino)-4-nitrobenzamide

HRID 410758Notes

Reaction equation

HRID 410758 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.C[CH2:16][N:17](C(C)C)C(C)C.CN>C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>[CH3:16][NH:17][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([NH:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 221846233-(Methylamino)-4-nitrobenzoic acid

Product 1

HCID 60144426N-methyl-3-(methylamino)-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 199401P,P-Diphenylphosphinic azideSolvent

Procedure

N-Methyl-3-methylamino-4-nitro-benzamide (407 mg) was prepared by following General Procedure N starting from 3-methylamino-4-nitro-benzoic acid (500 mg), DPPA (550 uL), DIEA (445 uL), and methylamine (2 M in THF, 2.55 mL).

Sources & evidence

ORD record
ord-7d2304e356624088a78609476118870f
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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