3,5-Dimethoxyaniline → 3a,4-Dihydro-6,8-dihydroxy-2H,3H-pyrrolo[1,2-a]quinoline-1,5-dione

HRID 2418804Notes

Reaction equation

HRID 2418804 reaction equation
O=[C:2]([CH2:9][CH2:10][C:11]([O:13]CC)=O)[CH2:3][C:4]([O:6]CC)=O.C[O:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([O:25]C)[CH:24]=1)[NH2:21]>>[OH:17][C:18]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:20]2[C:19]=1[C:4](=[O:6])[CH2:3][CH:2]1[CH2:9][CH2:10][C:11](=[O:13])[N:21]12

Participants

3

Reactant 2

HCID 663013,5-DimethoxyanilineHCID 81576Diethyl 3-oxoadipate

Product 1

HCID 133667053a,4-Dihydro-6,8-dihydroxy-2H,3H-pyrrolo[1,2-a]quinoline-1,5-dioneYield 77%

Procedure

By the procedures of Examples 2 and 3, diethyl 3-oxohexanedioate [Tetrahedron 23, p. 897 (1967)] and 3,5-dimethoxyaniline were converted to title product, recrystallized from ethyl acetate/cyclohexane, in 77% yield, m.p. 254°-256° C.; m/e 233 (m+); ir (KBr) 3448, 2857, 1680, 1639 cm-1.

Sources & evidence

ORD record
ord-b40a50f206064541932e072347a9c12a
Source dataset
uspto-grants-1984_09
Patent number
US04473704

Reaction notes

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