Hydrochloric Acid → HCID 70497265, Verbindung

HRID 1754145

Reaktionsgleichung

Reaktionsgleichung von HRID 1754145
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:21].[OH-].[Na+].[NH2:24][C:25]1[C:30]([F:31])=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]3[CH2:40][CH2:39]3)=[CH:34][CH:33]=2)[N:28]=[C:27]([C:41]([O:43]C)=[O:42])[C:26]=1[Cl:45].Cl>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]3[CH2:16][CH2:17]3)=[CH:13][CH:14]=2)[N:5]=[C:4]([C:18]([O:20][CH2:29][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:19])[C:3]=1[Cl:21].[NH2:24][C:25]1[C:30]([F:31])=[C:29]([C:32]2[CH:33]=[CH:34][C:35]([CH:38]3[CH2:39][CH2:40]3)=[CH:36][CH:37]=2)[N:28]=[C:27]([C:41]([OH:43])=[O:42])[C:26]=1[Cl:45]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70497242Methyl 4-amino-3-chloro-6-(4-cyclopropylphenyl)-5-fluoropicolinateHCID 70497265HCID 70497265, Verbindung

Produkt 2

HCID 70497265HCID 70497265, VerbindungAusbeute 94 %HCID 70497682Benzyl 4-amino-3-chloro-6-(4-cyclopropylphenyl)-5-fluoropicolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

4-Amino-3-chloro-6-(4-cyclopropylphenyl)-5-fluoropicolinic acid. A 2 M solution of aqueous NaOH (600 μL, 1.2 mmol, 2.0 equiv) was added to a stirred suspension of methyl 4-amino-3-chloro-6-(4-cyclopropylphenyl)-5-fluoropicolinate (190 mg, 0.59 mmol, 1.0 equiv) in methyl alcohol (3.0 mL) at 23° C. The resulting heterogeneous white mixture was stirred at 23° C. for 3 h. The reaction mixture was adjusted to approximately pH=4 via dropwise addition of concentrated HCl and then concentrated via rotary evaporation. The residue was slurried in water and vacuum filtered to afford the desired product, 4-amino-3-chloro-6-(4-cyclopropylphenyl)-5-fluoropicolinic acid as a white powder (170 mg, 94% yield): mp 147-149° C.; IR (thin film) 3463 (s), 3339 (s), 3202 (m), 3084 (w), 3007 (w), 1721 (m), 1630 (s) cm−1; 1H NMR (300 MHz, DMSO-d6) δ 7.70 (m, 2H), 7.17 (m, 2H), 6.81 (br s, 2H), 1.96 (m, 1H), 0.99 (m, 2H), 0.71 (m, 2H); ESIMS m/z 307 ([M+H]+).

Aufarbeitung

  1. concentrationconcentrated via rotary evaporation
  2. filtrationvacuum filtered

Quellen und Nachweise

ORD-Eintrag
ord-2b5dbb7143a44b13bb6caeca318a52ae
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169217B2

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