1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-3-methylbenzamide

HRID 473149Notes

Reaction equation

HRID 473149 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C([N:14]=C=NCCCN(C)C)C.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 781012-Amino-3-methylbenzoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 142218072-Amino-3-methylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-amino-3-methylbenzoic acid (1.5 g, 10 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (2.0 g, 13 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.3 g, 12 mmol), ammonium chloride (2.3 g, 42 mmol), and diisopropylethylamine (7.5 ml, 42 mmol). The mixture was purged with N2 and stirred for 60 h. The mixture was poured into water and extracte with EtOAc (50 mL×3), and the combined extracts were washed with brine (20 mL×2), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DCM and purified by silica gel chromatography eluting with 1:1 EtOAc/hexanes to afford 2-amino-3-methyl-benzamide as a white solid (1.3 g, 87%).

Workup

  1. customThe mixture was purged with N2
  2. additionThe mixture was poured into water and extracte with EtOAc (50 mL×3)
  3. washthe combined extracts were washed with brine (20 mL×2)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in DCM
  8. custompurified by silica gel chromatography
  9. washeluting with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-d891147177124c9db8d2109851b72d12
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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