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

HRID 445454Notes

Reaction equation

HRID 445454 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>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

4

Reactant 2

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

Product 1

HCID 1361757014-(2-Fluoro-4-nitrophenoxy)-7-hydroxy-6-methoxyquinolineYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a flask containing 7-benzyloxy-4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-quinoline (850 mg, 2.0 mmol) was added 20 mL of 30% HBr in AcOH. The resulted solution was stirred for 4 h at rt; at this time, a large amount of precipitate formed. The crude product was filtered, washed with Et2O and dried in air, giving 4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-7-hydroxyquinoline (609 mg, 92% yield).

Workup

  1. customat this time, a large amount of precipitate formed
  2. filtrationThe crude product was filtered
  3. washwashed with Et2O
  4. customdried in air

Sources & evidence

ORD record
ord-e7cc50a40fc14b0794bf0f5bdaa64431
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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