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

HRID 445439Notes

Reaction equation

HRID 445439 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>C(O)(=O)C.CCOCC>[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 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 120.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 7-benzyloxy-4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-quinoline (2.9 g, 6.9 mmol, 1.0 eq) and 33% HBr in acetic acid (30 ml). The mixture was stirred at room temperature for 3 hours and diluted with ether to give a pale white solid. The solid was filtered, washed with ether and dried to yield 4-(2-Fluoro-4-nitro-phenoxy)-6-methoxy-quinolin-7-ol as a pale white solid (2.74 g, 97.5% yield). 1H NMR (400 MHz, CDCl3): 11.89 (bs, 1H), 8.87 (d, 1H), 8.57 (d, 1H), 8.30 (d, 1H), 7.89 (m, 1H), 7.73 (s, 1H), 7.55 (s, 1H), 4.03 (s, 3H); MS (EI) for C16H11FN2O5: 421 (M+H+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customto give a pale white solid
  3. filtrationThe solid was filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-59da3a6a72424ad593a6fcbafa80a947
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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