Benzaldehyde → HCID 67377290, compound

HRID 877519Notes

Reaction equation

HRID 877519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11](S(C1C=CC(C)=CC=1)(=O)=O)[C:10]1[C:9](=[O:26])[CH2:8][CH2:7][CH2:6][C:5]2=1.[OH-].[K+].[C:29]1([CH:35]=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO>[CH:35](=[C:8]1[CH2:7][CH2:6][C:5]2[C:4]3[C:12](=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=3)[NH:11][C:10]=2[C:9]1=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 67362572HCID 67362572, compound2×

Product 1

HCID 67377290HCID 67377290, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 6,7-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (intermediate 1c) (0.8 g, 3.16 mmol) in MeOH (15 mL), KOH (53 mg, 0.94 mmol) followed by PhCHO (2.6 g, 24.5 mmol) were added. The reaction mixture was heated to 70-80° C. for 12 h. The solids were filtered and dried in vacuo to afford the title compound as a light yellow solid (0.75 g, 70%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 12.07 (s, 1H), 8.05 (s, 1H), 7.64 (d, J=13.0 Hz, 2H), 7.54 (d, J=7.0 Hz, 2H), 7.49-7.46 (m, 2H), 7.41 (d, J=7.5 Hz, 1H), 3.21-3.18 (m, 2H), 3.05-3.02 (m, 2H).

Workup

  1. additionwere added
  2. filtrationThe solids were filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d777fa8b5876497794745cb7fb4c5535
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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