Sodium Hydroxide → HCID 178422885, compound

HRID 2099433Notes

Reaction equation

HRID 2099433 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:12])[C:4]=2[N:3]=1.[NH:13]1[CH:17]=[C:16]([CH:18]=O)[N:15]=[CH:14]1.[OH-].[Na+]>OS(O)(=O)=O>[NH:13]1[CH:17]=[C:16]([CH:18]=[C:6]2[C:5](=[O:12])[C:4]3[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=3[CH2:8][CH2:7]2)[N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 764281H-Imidazole-4-carbaldehydeHCID 541706492-methyl-6,7-dihydroquinolin-8(5H)-one2×

Product 1

HCID 178422885HCID 178422885, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-methyl-6,7-dihydro-5H-quinolin-8-one (Intermediate 200A3) (15.1 g, 93.8 mmol) and imidazole-4-carbaldehyde (15 g, 156 mmol) in 40% H2SO4 (65 mL) was heated at 110° C. for 12 h. The reaction mixture was cooled to room temperature, poured onto crushed ice and basified with 2M NaOH until pH>8. The solids were collected on a glass frit, washed with water, dichloromethane and dried under vacuum to give unpurified 7-(1H-imidazol-4-yl-methylene)-2-methyl-6,7-dihydro-5H-quinolin-8-one (Intermediate 200A4) as a yellow solid, 22 g (98%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured
  3. customonto crushed ice
  4. customThe solids were collected on a glass frit
  5. washwashed with water, dichloromethane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a8cc795de79248b4abdf2e9fc23674fa
Source dataset
uspto-grants-2009_08
Patent number
US07569584B2

Reaction notes

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