Hydrogen Bromide → HCID 69874669, compound

HRID 353062Notes

Reaction equation

HRID 353062 reaction equation
C[O:2][C:3]1[C:12]2[CH:13]=[CH:14][O:15][C:11]=2[N:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.Br>CC(O)=O>[O:15]1[C:11]2=[N:10][C:9]3[C:4]([C:3](=[O:2])[C:12]2=[CH:13][CH2:14]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68085Dictamnine

Product 1

HCID 69874669HCID 69874669, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The hydrolysis of compound 1 with HBr in AcOH at 110° C. for 1 h gave furo[2,3-b]quinolin-4-one (2) with 36% yield (B. Klier, O. Schimmer, Mutagenesis 1999, 14, 181). The yield was increased up to 91% by refluxing the reaction mixture for 8 h. This improvement is crucial because the supply of starting dictamnine could be reduced.

Sources & evidence

ORD record
ord-4827a6f64a284d3bb8d5e59c91d1721e
Source dataset
uspto-grants-2004_06
Patent number
US06750223B2

Reaction notes

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