Acetic Acid → HCID 86732432, compound

HRID 1776402Notes

Reaction equation

HRID 1776402 reaction equation
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.C(O)(=O)C.[BrH:18]>>[Br:18][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 533933487-(Hydroxymethyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 86732432HCID 86732432, compound

Procedure

500 mg of 7-(hydroxymethyl)-3,4-dihydroquinolin-2(1H)-one (2.82 mmol, 1 eq.) were dissolved in 1.77 ml of 33% hydrogen bromide in glacial acetic acid (31.0 mmol, 11 eq.) under nitrogen atmosphere and stirred at room temperature for 30 minutes. The reaction mixture was partitioned between aq. saturated sodium hydrogen carbonate solution and dichloromethane/isopropanol 4+1. The aqueous layer was extracted three times with dichloromethane/isopropanol 4+1. The combined organic layers were washed with brine, dried over a silicone filter and concentrated in vacuo. The crude product was purified by flash chromatography to yield 175 mg (0.66 mmol, 23.3%) of the analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between aq. saturated sodium hydrogen carbonate solution and dichloromethane/isopropanol 4+1
  2. extractionThe aqueous layer was extracted three times with dichloromethane/isopropanol 4+1
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over a silicone
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography
  8. customto yield 175 mg (0.66 mmol, 23.3%) of the analytically pure target compound

Sources & evidence

ORD record
ord-029dcc361f7745f3b4fa41f3aa8f840a
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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