Hydrochloric Acid → 1,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

HRID 642922Notes

Reaction equation

HRID 642922 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH2:16]=O.Cl>CN(C=O)C>[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][C:11](=[CH2:16])[C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 117905051,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Accordingly, 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one was synthesized from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one using a formaldehyde reagent (paraformaldehyde), a mineral acid (HCl), and an ammonium salt (ammonium chloride) in an aprotic solvent (DMF). The ammonium salt appears to have had a positive impact on the rate of the reaction.

Workup

  1. customon the rate of the reaction

Sources & evidence

ORD record
ord-bdc26606a1b748f788f60af5d3a303a1
Source dataset
uspto-grants-2010_04
Patent number
US07696356B2

Reaction notes

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