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Benzylamine → N-benzyl-2-methyl-6-nitrobenzamide

HRID 631886
Notes
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Reaction equation

HRID 631886 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1.CCN(C(C)C)C(C)C.C(OCC)(=O)C>[CH2:14]([NH:21][C:6](=[O:8])[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 160976-Methyl-2-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 19805433N-benzyl-2-methyl-6-nitrobenzamideYield 75.5%

Reagents, catalysts & solvents 3

HCID 8857
Ethyl Acetate
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent
HCID 81531DiisopropylethylamineSolvent

Procedure

2-Nitro-6-methylbenzoic acid (0.91 g) and benzylamine (0.53 g) were dissolved in NMP (5 mL) and DIPEA (3 mL). HATU (1.9 g) was added and the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and then brine. The organic solution was dried with magnesium sulfate, filtered and the solvent was removed under vacuum to give a light brown oil (1.01 g) that crystallized on standing.

Workup

  1. washwashed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate
  2. dry with materialThe organic solution was dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-1218be025e15465492c80ea8cb1c6832
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes