Morpholine → 5-(Morpholin-4-yl)-2-nitrobenzoic acid

HRID 1985660Notes

Reaction equation

HRID 1985660 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].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(OCC)(=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 70640805-(Morpholin-4-yl)-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 5 g of 2-nitro-5-chlorobenzoic acid and 15 mL of morpholine 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 of water. The pH of the mixture is adjusted 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. Mp.: 172° C.

Workup

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

Sources & evidence

ORD record
ord-2e32272e170b4af5b1b7a9c0cd55b314
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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