Hydrochloric Acid → 3-Chloro-4-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

HRID 7255

Reaction equation

HRID 7255 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([F:22])[CH:15]=2)[C:3]=1[Cl:23].[NH:24]1C(=O)CC[C@H:25]1C(O)=O.Cl>>[Cl:23][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:22])[CH:15]=2)=[N:5][C:6]2[C:11]([C:2]=1[C:25]#[N:24])=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7405L-Pyroglutamic AcidHCID 220201954-Bromo-3-chloro-2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinoline

Product 1

HCID 1354891083-Chloro-4-cyano-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-olYield 41%

Procedure

This compound was prepared from 34b according to method F and method G (using Pyr./HCl). Yellow solid; Yield: 41% (for two steps); mp 325–328° C. (dec.); 1H-NMR (300 MHz, DMSO-d6) δ 7.10 (dd, J=8.8, 8.7 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.43 (dd, J=8.4, 1.4 Hz, 1H), 7.49 (dd, J=9.2, 2.5 Hz, 1H), 7.55 (dd, J=12.2, 2.0 Hz, 1H), 8.04 (d, J=9.1 Hz, 1H), 10.37 (s, 1H), 10.97 (s, 1H); MS (ESI) m/z 313 ([M−H]−), 315 ([M+H]+); Anal. Calcd for C16H8ClFN2O2: C: 61.07, H: 2.56, N: 8.90. Found: C: 60.80, H: 2.57, N: 8.55.

Sources & evidence

ORD record
ord-2b0d9ce6dac1428494fdac9548bda8fb
Source dataset
uspto-grants-2006_08
Patent number
US07084276B2

Linked notes

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