Morpholine → Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

HRID 1623727Notes

Reaction equation

HRID 1623727 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].C(N(C(C)C)CC)(C)C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O.C(OCC)(=O)C.C(Cl)CCl>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:8])=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

9

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 132228014-Hydroxy-3-(methoxycarbonyl)benzoic acid

Product 1

HCID 67107453Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-3-[(methyloxy)carbonyl]benzoic acid (may be prepared as described in Description 107, 1.31 g, 6.68 mmol) in N,N-dimethylformamide (10 ml) was added diisopropylethylamine (2.33 ml, 13.36 mmol), morpholine (1.75 ml, 20.03 mmol), HOBT (1.33 g, 8.68 mmol) and EDC (2.56 g, 13.36 mmol). The solution was stirred at room temperature for 18 hours then another equivalent of EDC was added (1.28 g, 13.38 mmol). The solution was stirred for another 6 hours then ethyl acetate (20 ml) and water were added. The organic layer was separated, washed with water (3×10 ml), dried (MgSO4) and the solvent removed in vacuo to give a gum. Purification by MDAP yielded the title compound as a gum. 560 mg.

Workup

  1. stirringThe solution was stirred for another 6 hours
  2. customThe organic layer was separated
  3. washwashed with water (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a gum
  7. customPurification by MDAP

Sources & evidence

ORD record
ord-1c86fd1c1a474945b3174b2d16980957
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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