Sodium Carbonate → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol

HRID 582868Notes

Reaction equation

HRID 582868 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2[C:7]([NH:10][CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+]>Br>[N:13]1([CH2:12][CH2:11][NH:10][C:7]2[C:6]3[CH:19]=[CH:20][C:3]([OH:2])=[CH:4][C:5]=3[O:9][N:8]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 187964566-Methoxy-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine

Product 1

HCID 1358150593-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-olYield 36.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Methoxy-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine (2.9 g) was dissolved in 48% hydrobromic acid (50 ml) and heated to reflux under nitrogen for 3 hours. The reaction was cooled to room temperature, neutralized with saturated sodium carbonate (Na2CO3) solution, and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 3:2 acetone/heptane and subsequently titration with DCM/heptane provided the product (1.0 g), m.p. 151-152° C.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 3 hours
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography (silica gel) eluting with 3:2 acetone/heptane and subsequently titration with DCM/heptane

Sources & evidence

ORD record
ord-88685e70a552479f9f31d692c4588456
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Reaction notes

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