N-methyl-2-pyrrolidone → 4'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 1669871Notes

Reaction equation

HRID 1669871 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21]([C:28]([OH:30])=O)[CH:20]=2)=[CH:15][CH:14]=1.C1C=[CH:33][C:34]2[N:39](O)N=N[C:35]=2C=1.CN1[C:46](=[O:47])CCC1>C(Cl)Cl.CN(C=O)C>[CH3:46][O:47][CH2:33][CH:34]([NH:39][C:28]([C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([CH3:12])=[CH:18][CH:17]=2)[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=1)=[O:30])[CH3:35]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 532248984'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 595997024'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amideYield 83.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (16.17 g, 84.38 mmol) was added portion wise to a stirred solution of 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (15.49 g, 60.27 mmol), HOBt (11.44 g, 84.38 mmol) and 2-amino-1-methoxy-1-propane (7 ml, 66.31 mmol) in NMP (9.29 ml, 84.38 mmol), CH2Cl2 (180 ml) and DMF (20 ml) at 0° C. The mixture was allowed to warm to room temperature and was stirred at the same temperature for 14 hours. The reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as a yellow oil (16.5 g, 83.5%). MS (M+H)=329.

Workup

  1. washThe reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-94a735b8e1bd49abbff44cff857521dd
Source dataset
uspto-grants-2011_08
Patent number
US07989637B2

Reaction notes

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