Hydrogen Bromide → 4-(2-Fluoro-4-nitrophenoxy)-7-hydroxy-6-methoxyquinoline

HRID 15518Notes

Reaction equation

HRID 15518 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.Br.CCOCC>CC(O)=O>[F:29][C:21]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=1[O:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:30][CH3:31])[CH:11]=2)[N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 229354107-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

Product 1

HCID 1361757014-(2-Fluoro-4-nitrophenoxy)-7-hydroxy-6-methoxyquinolineYield 124.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline (2.20 g, 5.24 mmol) and HBr in HOAc (3 mL of 33% solution) was allowed to stay at rt for 4 h. Ether (35 mL) was added to the reaction mixture, stirred for 20 minutes, and the solid was filtered and dried to obtain the product (2.15 g, 100%) as a beige-colored HBr salt solid. 1H NMR (CD3OD) δ 8.69 (d, 1H, J=6.6 Hz), 8.41 (dd, 1H, J=9.9, 2.8 Hz), 8.33 (dd, 1H, J=8.8, 1.7 Hz), 7.84 (m, 2H), 7.43 (s, 1H), 7.05 (d, 1H, J=6.1 Hz), 4.13 (s, 3H).

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-c729436a91ac430285d667a3b923c77a
Source dataset
uspto-grants-2010_06
Patent number
US07732613B2

Reaction notes

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