Methanol → 2-Morpholin-4-ylmethyl-6-nitro-benzoic acid

HRID 2042851Notes

Reaction equation

HRID 2042851 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[OH-].[Na+].CO.C1COCC1>O>[N:14]1([CH2:13][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=2[C:3]([OH:20])=[O:2])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 598410552-Morpholin-4-ylmethyl-6-nitro-benzoic acid methyl ester

Product 1

HCID 598410692-Morpholin-4-ylmethyl-6-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 5 (0.85 g) and NaOH (0.304 g) in a mixture of water (9 mL), methanol (5 mL), and THF (45 mL) was stirred at reflux for 24 h and concentrated to dryness. The residue was dissolved in water, and the solution was cooled to 0° C. and adjusted to pH 7 with 10% potassium hydrogen sulfate. The mixture was concentrated to dryness, the residue was treated with methanol, and filtered to remove solids. The filtrate was concentrated to yield compound 6 as a yellow solid.

Workup

  1. temperatureat reflux for 24 h
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in water
  4. concentrationThe mixture was concentrated to dryness
  5. additionthe residue was treated with methanol
  6. filtrationfiltered
  7. customto remove solids
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9c84e33481cb40e7ae71d2719f89f07f
Source dataset
uspto-grants-2013_11
Patent number
US08586597B2

Reaction notes

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