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

HRID 852517Notes

Reaction equation

HRID 852517 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([NH2:21])[CH:13]=1.CCN(CC)CC>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([NH:21][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 740895-Chlorovaleryl chlorideHCID 2756518Methyl 3-amino-5-nitrobenzoate

Product 1

HCID 693570733-(5-Chloro-pentanoylamino)-5-nitro-benzoic acid methyl esterYield 124.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chlorovaleryl chloride (2.64 g, 17 mmol, 1.1 equiv) in CH2Cl2 (5 ml) was added over 2 min to a stirred solution of 3-amino-5-nitro-benzoic acid methyl ester (D1) (3 g, 15.3 mmol, 1 equiv) and NEt3 (2.6 ml, 18 mmol, 1.2 equiv) in CH2Cl2 (30 ml). The resulting mixture was stirred for 1 h at room temperature then washed with 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with CH2Cl2 to give 3-(5-Chloro-pentanoylamino)-5-nitro-benzoic acid methyl ester D3 (6 g, 112%) as a brown oil.

Workup

  1. washthen washed with 2N aqueous HCl solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-9759496f4dff403ea5fab7ba35909980
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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