Benzaldehyde → HCID 67377908, compound

HRID 877516Notes

Reaction equation

HRID 877516 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:16])[C:9]=1[NH:10]2.[OH-].[K+].[C:19]1([CH:25]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH:25](=[C:7]1[CH2:6][CH2:5][C:4]2[C:3]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:15])[C:2]=3[Cl:1])[NH:10][C:9]=2[C:8]1=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 67377640HCID 67377640, compound2×

Product 1

HCID 67377908HCID 67377908, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5,6-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (intermediate 5a) (0.8 g, 1.97 mmol) in MeOH (10 mL), KOH (0.055 g, 0.98 mmol) followed by PhCHO (1.0 g, 9.42 mmol) were added. The reaction mixture was heated to 80° C. for 12 h cooled to room temperature during which a solid precipitated out which was filtered and dried in vacuo to give the title compound as a light yellow solid (0.7 g, 70%). 1H NMR (500 MHz, CDCl3, δ in ppm) 9.25 (bs, 1H), 7.80 (s, 1H), 7.45-7.42 (m, 4H), 7.39-7.35 (m, 2H), 7.31 (d, J=9.0 Hz, 1H), 3.44 (t, J=6.0 Hz, 2H), 3.28 (t, J=6.0 Hz, 2H).

Workup

  1. additionwere added
  2. temperaturecooled to room temperature during which a solid
  3. customprecipitated out which
  4. filtrationwas filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6291bc5569a943b4baaebebae8ffb4bc
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

Loading…