Pivaloyl chloride → 2-Amino-3-(2,2-dimethylpropionylamino)benzoic acid methyl ester

HRID 388802Notes

Reaction equation

HRID 388802 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11].[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=[O:16]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:15](=[O:16])[C:14]([CH3:19])([CH3:18])[CH3:13])[C:5]=1[NH2:11]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 593842222-Amino-3-(2,2-dimethylpropionylamino)benzoic acid methyl esterYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2,3-diaminobenzoic acid methyl ester (2.3 g, 13.8 mmol) in pyridine (40 mL) at room temperature was added 2,2-dimethylpropionyl chloride (1.7 g, 14.0 mmol). The solution was stirred at for 16 h, evaporated, and the residue partitioned between ethyl acetate (100 mL) and 1M aqueous hydrochloric acid (100 mL). The organic phase was separated, washed with 1M aqueous hydrochloric acid (100 mL), dried over sodium sulfate and evaporated to afford the title compound as a dark oil (2.7 g, 10.8 mmol, 78%) which was used without further purification. (m/z): [M+H]+ calcd for C13H18N2O3 251.14. found 250.8

Workup

  1. customevaporated
  2. customthe residue partitioned between ethyl acetate (100 mL) and 1M aqueous hydrochloric acid (100 mL)
  3. customThe organic phase was separated
  4. washwashed with 1M aqueous hydrochloric acid (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f194e1dc75f74c92a0cc08d0d165ef17
Source dataset
uspto-grants-2013_02
Patent number
US08377964B2

Reaction notes

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