1,3-Benzodioxol-4-amine → 3-Cyano-7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline

HRID 1784097Notes

Reaction equation

HRID 1784097 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[CH2:17]1[O:26][C:25]2[C:19](=[C:20]([CH:22]=[CH:23][CH:24]=2)[NH2:21])[O:18]1>C(O)CC>[C:15]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[C:25]3[O:26][CH2:17][O:18][C:19]=13)=[CH:10][C:9]([O:12][CH3:13])=[C:8]([OH:14])[CH:7]=2)#[N:16]

Participants

4

Reactant 2

HCID 103131651,3-Benzodioxol-4-amineHCID 1357436694-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 1354941593-Cyano-7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 4-chloro-3-cyano-7-hydroxy-6-methoxyquinoline (5 g), 2,3-methylenedioxyaniline (3.07 g) and propanol (100 ml) was stirred and heated to 115° C. for 18 hours. The resultant precipitate was isolated, washed in turn with propanol and diethyl ether and dried under vacuum. There was thus obtained the title compound (5.51 g); NMR Spectrum: (DMSOd6) 3.99 (s, 3H), 6.06 (s, 2H), 6.93-7.0 (m, 3H), 7.48 (s, 1H), 8.16 (s, 1H), 8.94 (s, 1H); Mass Spectrum: M+H+ 336.

Sources & evidence

ORD record
ord-a69c7a0cf7e74c18b0e09732f80e77bf
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

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