Acetic Acid → 6-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023179Notes

Reaction equation

HRID 1023179 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.C(O)(=O)C.[Br-:21].[Li+]>C1COCC1>[Br:21][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 82050Lithium BromideHCID 145174016-(Oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 866804246-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-oneYield 10,085.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one (0.2 g, 0.909 mmol) in dry THF (5 mL) was added acetic acid (0.162 g, 2.272 mmol) and lithium bromide (0.118 g, 1.363 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated to remove solvent and water was added (25 mL). The solid was filtered and dried to give crude 6-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one as an off-white solid (0.25 g, 91.675 mmol). LCMS: RT 0.65 min; LCMS (ES-API), m/z 300.0 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove solvent and water
  3. additionwas added (25 mL)
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-867f36281d0c46f3aa3ba206c3c75461
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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