Morpholine → Methyl 3-amino-5-morpholino-2-nitrobenzoate

HRID 85138Notes

Reaction equation

HRID 85138 reaction equation
[NH2:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9](Cl)[CH:10]=1)[C:5]([O-:7])=[O:6].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:10]=1)[C:5]([O:7][CH3:21])=[O:6]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 672009403-Amino-5-chloro-2-nitrobenzoate

Product 1

HCID 58278827Methyl 3-amino-5-morpholino-2-nitrobenzoateYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 3-amino-5-chloro-2-nitrobenzoate (71; 3.3 g, 14.35 mmol) in DMF (66 ml) was added morpholine (48; 7.12 g, 81.78 mmol) and K2CO3 (11.28 g, 81.78 mmol). The resulting reaction mixture was stirred at 105° C. for 4 h. It was then filtered, diluted with water (500 ml), and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Column chromatography afforded methyl 3-amino-5-morpholino-2-nitrobenzoate 72 (2.1 g, 52.1%) as a brown yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. filtrationIt was then filtered
  3. additiondiluted with water (500 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c446e10fce94757acaca3d13a84923a
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

Loading…