Triethylamine → 5-Amino-N-methyl-N-propyl-isophthalamic acid methyl ester

HRID 732512Notes

Reaction equation

HRID 732512 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.Cl.[CH3:18][N:19](C)[CH2:20][CH2:21][CH2:22]N=C=NCC.ON1C2C=CC=CC=2N=N1.C(NC)CC.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([NH2:13])[CH:10]=[C:6]([C:7]([N:19]([CH3:18])[CH2:20][CH2:21][CH3:22])=[O:9])[CH:5]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 12315N-MethylpropylamineHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl esterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 688147595-Amino-N-methyl-N-propyl-isophthalamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 5-nitro-isophthalic acid monomethylester (3.0 g, 13.32 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.20 g, 16.65 mmol), and 1-hydroxybenzotriazole (2.25 g, 16.65 mmol) in dichloromethane (100 mL) at room temperature for 20 min. Add propylmethylamine (1.46 g, 16.65 mmol) and triethylamine (3.36 g, 33.3 mmol). Stir at room temperature for 1 h, dilute with ethyl acetate, wash with 10% aqueous potassium carbonate, 1 N citric acid, saturated aqueous sodium chloride and concentrate. Dissolve in ethanol (100 mL), add a slurry of 10% Pd/C (300 mg) in ethanol (10 mL) and place under a hydrogen atmosphere using a balloon and stir overnight. Flush with nitrogen, filter and concentrate to give the title compound as an oil.

Workup

  1. washwash with 10% aqueous potassium carbonate, 1 N citric acid, saturated aqueous sodium chloride
  2. concentrationconcentrate
  3. dissolutionDissolve in ethanol (100 mL)
  4. additionadd a slurry of 10% Pd/C (300 mg) in ethanol (10 mL) and place under a hydrogen atmosphere
  5. stirringstir overnight
  6. customFlush with nitrogen
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-128409f2b31b4ccfa2514dc96fbce979
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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