Triethylamine → 3-(4-Chloro-butanoylamino)-5-nitro-benzoic acid methyl ester

HRID 852516Notes

Reaction equation

HRID 852516 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([NH2:13])[CH:5]=1.CCN(CC)CC.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([NH:13][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][Cl:22])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 2756518Methyl 3-amino-5-nitrobenzoate

Product 1

HCID 693563003-(4-Chloro-butanoylamino)-5-nitro-benzoic acid methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-5-nitro-benzoic acid methyl ester (D1) (38 g, 194 mmol, 1 equiv) in CH2Cl2 (350 ml) was added NEt3 (32 ml, 230 mmol, 1.2 equiv) followed by 4-chlorobutyryl chloride (24.7 ml, 220 mmol, 1.13 equiv) dropwise over 20 nm. The resulting mixture was allowed to warm to room temperature and stirred for 30 min. The organic phase was then washed with 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with iso-hexane and Et2O to give 3-(4-chloro-butanoylamino)-5-nitro-benzoic acid methyl ester D2 (56 g, 96%) as a brown solid.

Workup

  1. washThe organic phase was then washed with 2N aqueous HCl solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with iso-hexane and Et2O

Sources & evidence

ORD record
ord-e66e8a5bf74f471e8410e2e138b2356e
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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