5-Chloro-2-nitrobenzoic acid → 5-(2,6-Dimethylmorpholin-4-yl)-2-nitrobenzoic acid

HRID 2195685Notes

Reaction equation

HRID 2195685 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH3:14][CH:15]1[O:20][CH:19]([CH3:21])[CH2:18][NH:17][CH2:16]1>C(OCC)(=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:17]2[CH2:16][CH:15]([CH3:14])[O:20][CH:19]([CH3:21])[CH2:18]2)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 172865-Chloro-2-nitrobenzoic acidHCID 1108622,6-Dimethylmorpholine

Product 1

HCID 431767115-(2,6-Dimethylmorpholin-4-yl)-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 5 g 2-nitro-5-chlorobenzoic acid and 15 ml 2,6-dimethylmorpholine is stirred at 120° C. for 6 hours. To the reaction mixture 150 ml of ethyl acetate is added. The precipitated yellow crystalline material is filtered off, dissolved in 15 ml water. The pH of the mixture is set to 6 with acetic acid. The precipitated material is filtered off, washed with water and dried, to obtain 4.2 g of the title compound (MH+:281).

Workup

  1. filtrationThe precipitated yellow crystalline material is filtered off
  2. dissolutiondissolved in 15 ml water
  3. filtrationThe precipitated material is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c9c98bfa0ef44ede9b32351e87a977b1
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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