Hydrochloric Acid → 7-Hydroxy-3,4-dihydrocarbostyril

HRID 1244029Notes

Reaction equation

HRID 1244029 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=1)=[O:9].Cl>>[OH:17][C:13]1[CH:12]=[C:11]2[C:16]([CH2:6][CH2:7][C:8](=[O:9])[NH:10]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 27857563-chloro-N-(3-methoxyphenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27857587-Hydroxy-3,4-dihydrocarbostyrilYield 55%

Conditions

Temperature
200 °C

Procedure

Under nitrogen with outlet to back of hood, added 12.37 g of aluminum chloride powder (0.093 mol) to 7.93 g of 3-Chloro-N-(3-methoxy-phenyl)-propionamide (0.037 mol). Placed in preheated 160° C. sand bath, and heated for 4 hours, raising bath temperature to 200° C., until no more HCl is observed. Cooled to room temperature, chilled in ice bath and cautiously added ice-H2O. Extracted three times with EtOAc, dried (MgSO4), and evaporated under reduced pressure. Purified by flash chromatography on 230–400 Å mesh silica gel, eluting with 1:1 EtOAc/Hexanes to give 3.3 g of beige solid (55%). 1H NMR (400 MHz, CDCl3) δ 2.60 (2H, q, J=6.23 Hz), 2.88 (2H, t, J=6.85 Hz), 6.23 (1H, d, J=2.49 Hz), 6.44 (1H, q, J=2.49 Hz), 7.00 (1H, d, J=8.09 Hz). M/z (APCI+) 163.7 (M+1).

Workup

  1. customUnder nitrogen with outlet to back of hood
  2. customPlaced in preheated 160° C.
  3. temperatureheated for 4 hours
  4. temperatureCooled to room temperature
  5. temperaturechilled in ice bath
  6. extractionExtracted three times with EtOAc
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customPurified by flash chromatography on 230–400 Å mesh silica gel
  10. washeluting with 1:1 EtOAc/Hexanes

Sources & evidence

ORD record
ord-3ca28b7a947f433caf2432051d3913a9
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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