Benzoyl chloride, 3-nitro- → HCID 9868369, compound

HRID 1357380Notes

Reaction equation

HRID 1357380 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:13][O:14][C:15](=[O:34])[C:16]1[C:17](=[CH:22][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH2:33])=[CH:24][CH:25]=1)[C:18]([O:20][CH3:21])=[O:19]>CC(C)=O>[CH3:13][O:14][C:15](=[O:34])[C:16]1[C:17](=[CH:22][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH:33][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:24][CH:25]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 16641022HCID 16641022, compound

Product 1

HCID 9868369HCID 9868369, compoundYield 126.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 3-nitrobenzoyl chloride (0.43 g, 2.3 mmol) in dry acetone (2ml) was added slowly to a solution of 4-(2-aminophenoxy)phthalic acid dimethyl ester (0.63 g, 2.09 mmol) and TEA (0.35 ml, 2.5 mmol) in dry acetone (2ml) at 0° C. The mixture was stirred at room temperature for 20 hours, filtered and the filtrate evaporated to dryness in vacuo. The crude product was purified on silica gel (eluent: methylene chloride/ethyl acetate (95:5)) to give 4-[2-(3-nitrobenzoylamino)phenoxy]phthalic acid dimethyl ester (yield: 1.19 g (47%)) as a golden oil. 1H—NMR (CDCl3) in ppm: δ 3.9 (6H,2xs); 7.02 (1H,d.d.); 7.1-7.25 (2H,m); 7.25-7.35 (2H,m); 7.7 (1H,t); 7.83 (1H,d); 8.1 (1H,d.t.); 8.3 (1H, broad s); 8.4 (1H,m); 8.54 (1H,d.d.); 8.65 (1H,m).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness in vacuo
  3. customThe crude product was purified on silica gel (eluent: methylene chloride/ethyl acetate (95:5))

Sources & evidence

ORD record
ord-521c2e900cb44a3f8db897fd30abfea0
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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