Hydrochloric Acid → HCID 59631038, compound

HRID 2099446Notes

Reaction equation

HRID 2099446 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=2)[C:10]([O:12]C)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[CH3:21][NH2:22].C([Al](CC)CC)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[N:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=2)[C:10]([NH:22][CH3:21])=[O:12])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6364545Methylamine hydrochlorideHCID 16682930TriethylaluminumHCID 59631412HCID 59631412, compound

Product 1

HCID 59631038HCID 59631038, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
60 °C

Procedure

A stirred solution of 3-(4-morpholinyl)-5-nitro-benzoic acid, methyl ester (Example 86c; 0.53 g, 2 mmol) in toluene (5 mL) under an argon atmosphere, is treated with a mixture of methylamine hydrochloride (0.27 g, 4 mmol), triethylaluminium (2 mL of a 2 M solution in toluene, 4 mmol) in toluene (5 mL) and heated at 60° C. for 18 h. The cooled mixture is then treated with hydrochloric acid (10 mL of 2 M), stirred for 5 min and then treated with aqueous sodium hydroxide (5 mL of 4 M). The mixture is then treated with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with brine (2×50 mL), dried (MgSO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ethyl acetate to afford the title compound as yellow crystalline solid, m.p. 204-207° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts are washed with brine (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent is evaporated off under reduced pressure
  5. customto give the crude product which
  6. customis purified by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-5cea00e37f504e0c940080b3cbcb0a2b
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

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