Dimethylformamide dimethyl acetal → 2-Dimethylaminomethylene-5-(2-methoxy-phenyl)-cyclohexane-1,3-dione

HRID 2046457Notes

Reaction equation

HRID 2046457 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[CH2:10]1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].ClC1C=CC(C2CC(=O)C(=CN(C)C)C(=O)C2)=CC=1>>[CH3:19][N:20]([CH:22]=[C:12]1[C:11](=[O:16])[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][C:13]1=[O:15])[CH3:21]

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 5670705-(4-Chlorophenyl)-2-[(dimethylamino)methylene]-1,3-cyclohexanedioneHCID 171223135-(2-Methoxyphenyl)-1,3-cyclohexanedione

Product 1

HCID 582693772-Dimethylaminomethylene-5-(2-methoxy-phenyl)-cyclohexane-1,3-dione

Procedure

The title compound was prepared from 5-(2-methoxy-phenyl)-cyclohexane-1,3-dione (386 mg, 1.77 mmol), example 1/a, and N,N-dimethylformamide dimethylacetal (2 ml), following the procedure described for 5-(4-chloro-phenyl)-2-dimethylaminomethylene-cyclohexane-1,3-dione (example 2/a stage 1) except that the reaction was run at 100° C. for 2 h, after which the solvent was removed by evaporation under reduced pressure to produce the title compound as a brown oil. The title compound was used without further purification in the next step.

Workup

  1. customafter which the solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7315d5875af74fd98f60a4d51d911152
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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