Morpholine → 5-Bromo-2-hydroxy-4-(4-morpholinylmethyl)benzoic acid

HRID 2204676Notes

Reaction equation

HRID 2204676 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C([O:17][C:18]1[CH:27]=[C:26]([CH2:28]Br)[C:25]([Br:30])=[CH:24][C:19]=1[C:20]([O:22]C)=[O:21])(=O)C>CC(C)=O>[Br:30][C:25]1[C:26]([CH2:28][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:27][C:18]([OH:17])=[C:19]([CH:24]=1)[C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 66611269Methyl 2-(acetyloxy)-5-bromo-4-(bromomethyl)benzoate

Product 1

HCID 666113505-Bromo-2-hydroxy-4-(4-morpholinylmethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Triethylamine (0.37 ml, 2.63 mmol) and morpholine (0.15 ml, 1.71 mmol) were added to a solution of methyl 2-(acetyloxy)-5-bromo-4-(bromomethyl)benzoate (may be prepared as described in Description 4; 481 mg, 1.31 mmol) in acetone (10 ml). The mixture was stirred for 30 minutes then the solvent was removed in vacuo. The residue was redissolved in dichloromethane (10 ml), washed with water (10 ml), dried (MgSO4) and the solvent removed in vacuo to give the morpholine intermediate.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in dichloromethane (10 ml)
  3. washwashed with water (10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8d9ae7e836a14ba7bc2e2f5eee8c6d20
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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