Acetic Anhydride → 2-Acetylpyrrolo[3,4-g]quinoline

HRID 654741Notes

Reaction equation

[N:1]1[C:10]2[CH:9]=[C:8]3[CH:11]=[N:12][CH:13]=[C:7]3[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N[CH2:15][C:16]([O-])=[O:17].[K+].C(OC(=O)C)(=O)C>>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3=[CH:13][N:12]=[CH:11][C:8]3=[CH:9][C:10]=2[N:1]=1)(=[O:17])[CH3:15]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 23673715Potassium glycinate

HCID 67915813Pyrrolo[3,4-g]quinoline

Product 1

HCID 679157682-Acetylpyrrolo[3,4-g]quinoline

Procedure

The pyrrolo[3,4-g]quinoline derivatives of formula (1) and (2) are prepared by reacting a 7-dimethylaminomethylene-6-oxo-trans-quinoline derivative of formula (7a) or (7b) with potassium glycinate, followed by treatment of the thus formed intermediate product with acetic anhydride. This yields a 2-acetylpyrrolo[3,4-g]quinoline compound. The acetyl group is removed by basic hydrolysis, for example using sodium ethoxide in ethanol. Preparation of the pyrrolo3,4-g]-quinolines of formula (1) is illustrated in Reaction Scheme III: ##STR17## The pyrrolo[3,4-g]quinolines of formula (2) are prepared using the same procedure and starting materials of formula (7b).

Workup

customare prepared

Sources & evidence

ORD record: ord-e43abcc73d634d5191967b0e927c0dba
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05134143

Reaction notes

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