3-chloro-N-(4-hydroxyphenyl)propanamide → 6-Hydroxy-3,4-dihydro-2(1H)-quinolinone

HRID 1014291Notes

Reaction equation

HRID 1014291 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-]>>[OH:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 30083813-chloro-N-(4-hydroxyphenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneYield 80.4%

Conditions

Temperature
180 °C

Procedure

A mixture of 3-chloro-N-(4-hydroxyphenyl)propanamide (122 g, 0.61 mol) and AlCl3 (327 g, 2.45 mol) were slowly heated with vigorous stirring at 180° C. (a thick melt formed) and after 5 hours the liquid was poured over ice. The solids were collected by filtration, washed with water, and recrystallized from MeOH to afford 6-hydroxy-3,4-dihydro-2(1 H)-quinolinone (80 g, 40% yield). 1H NMR (400 MHz, DMSO) δ, 2.32-2.36 (m, 2 H), 2.74 (t, 2 H, J=7.2 Hz), 6.50 (m, 1 H), 6.54 (d, 1 H, J=2.8 Hz), 662(d, 1 H, J=8.4 Hz), 9.00 (br, 1 H), 9.78 (br, 1 H).

Workup

  1. temperaturewere slowly heated
  2. customformed) and after 5 hours the liquid
  3. additionwas poured over ice
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-45f5b828d2fe406889ac10f4af21435e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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