Piperonal → 3-(3,4-Methylenedioxyphenyl)-6-dimethylaminophthalide

HRID 569679Notes

Reaction equation

HRID 569679 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[O:2]1.[CH3:12][N:13]([CH3:23])[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18].C(N(CC1C=CC=CC=1)C1C=CC(C2C3C(=CC(N(C)C)=CC=3)C(=O)O2)=CC=1)C>C(OC(=O)C)(=O)C>[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]3[C:20]4[C:16](=[CH:15][C:14]([N:13]([CH3:23])[CH3:12])=[CH:22][CH:21]=4)[C:17](=[O:18])[O:7]3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 668373-(Dimethylamino)benzoic acidHCID 540434433-[4-(N-ethylbenzylamino)phenyl]-6-dimethylaminophthalide

Product 1

HCID 136517333-(3,4-Methylenedioxyphenyl)-6-dimethylaminophthalideYield 6.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Following a procedure similar to that described in Example 1, part A above, 7.5 g of 3,4-(methylenedioxy)benzaldehyde and 9.1 g of 3-dimethylaminobenzoic acid were interacted in acetic anhydride to obtain 0.9 g of 3-(3,4-methylenedioxyphenyl)-6-dimethylaminophthalide (Formula II: R=CH3 ; X=H; Y=1-[3,4-(OCH2O)C6H3 ]) a light yellow solid melting over the range 134°-143° C.

Sources & evidence

ORD record
ord-04041833d8d743f3a10e64c0be38e71d
Source dataset
uspto-grants-1988_03
Patent number
US04732991

Reaction notes

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