Dipropylamine → Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

HRID 852562Notes

Reaction equation

HRID 852562 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.C(Cl)(C(Cl)=O)=O.[CH2:23]([NH:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:6]([C:7]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])=[O:9])[CH:5]=1

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 65578Oxalyl chlorideHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

Product 1

HCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoateYield 110%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-nitro-isophthalic acid monomethyl ester (D77) (1.0 g, 4.44 mmol, 1 equiv) in CH2Cl2 (40 ml) was treated with (COCl)2 (655 mg, 5.2 mmol, 1.2 equiv) followed by a few drops of DMF. The resulting mixture was stirred for 1 h at room temperature and then dipropylamine (1.65 g, 15 mmol, 3.4 equiv) was added and the resulting solution stirred for a further 30 min. The solution was then washed with 2N aqueous HCl solution (50 ml), saturated aqueous NaHCO3 solution (50 ml), dried over MgSO4 and concentrated in vacuo to give 5-nitro-N,N-dipropyl-isophthalamic acid methyl ester (D87) (1.5 g, 110%) as a pale yellow oil.

Workup

  1. stirringthe resulting solution stirred for a further 30 min
  2. washThe solution was then washed with 2N aqueous HCl solution (50 ml), saturated aqueous NaHCO3 solution (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a8f94d2f70d4827bc3616cadcde2c0f
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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