Hydrogen Bromide → HCID 66733495, compound

HRID 1664292Notes

Reaction equation

HRID 1664292 reaction equation
Br.C([O:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[C:11]([O:20]C)[C:12]([F:19])=[C:13]([F:18])[CH:14]=2)[N:9]([CH2:22][CH3:23])[CH:8]=1)=[O:6])C.O>CC(O)=O>[CH2:22]([N:9]1[C:10]2[C:15](=[CH:14][C:13]([F:18])=[C:12]([F:19])[C:11]=2[OH:20])[C:16](=[O:17])[C:7]([C:5]([OH:6])=[O:4])=[CH:8]1)[CH3:23]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 14099128HCID 14099128, compound

Product 1

HCID 66733495HCID 66733495, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

48% aq. HBr (35 ml) was added to a solution of 1-ethyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (9.34 g; prepared according to EP 241 206) in AcOH (30 ml). The orange solution was stirred at 110° C. for 24 h. It was poured into water (200 ml) and the grey-white precipitate was filtered. The crystals were collected and dried in vacuo to afford 6.37 g (79% yield) of a beige solid. 1H NMR (DMSOd6; δ ppm): 1.43 (3H, t, J=7); 4.85 (2H, q, J=7); 7.76 (1H, dd, J=8 and J=10); 8.91 (1H, s); 12.02 (1H, broad); 14.90 (1H, broad).

Workup

  1. filtrationthe grey-white precipitate was filtered
  2. customThe crystals were collected
  3. customdried in vacuo

Sources & evidence

ORD record
ord-dfecc2f12aaa4cd09d05553eaea080d3
Source dataset
uspto-grants-2011_10
Patent number
US08039466B2

Reaction notes

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