Hydrochloric Acid → 4-Amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinic acid

HRID 1754143노트

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HRID 1754143 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH2:17][CH3:18])[C:10]=2[F:19])[N:5]=[C:4]([C:20]([OH:22])=[O:21])[C:3]=1[Cl:23].[OH-].[Na+].[NH2:26][C:27]1[C:32]([F:33])=[C:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([O:41][CH2:42][CH3:43])[C:35]=2[F:44])[N:30]=[C:29]([C:45]([O:47]C)=[O:46])[C:28]=1[Cl:49].Cl>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH2:17][CH3:18])[C:10]=2[F:19])[N:5]=[C:4]([C:20]([O:22][CH2:31][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:21])[C:3]=1[Cl:23].[NH2:26][C:27]1[C:32]([F:33])=[C:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([O:41][CH2:42][CH3:43])[C:35]=2[F:44])[N:30]=[C:29]([C:45]([OH:47])=[O:46])[C:28]=1[Cl:49]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 704976164-Amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinic acidHCID 70498279Methyl 4-amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinate

생성물 2

HCID 57412075Benzyl 4-amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinateHCID 704976164-Amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinic acid수율 88%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
23 °C

실험 절차

4-Amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinic acid. A 2 M solution of aqueous NaOH (900 μL, 1.8 mmol, 4.0 equiv) was added to a stirred suspension of methyl 4-amino-3-chloro-6-(4-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinate (170 mg, 0.45 mmol, 1.0 equiv) in methyl alcohol (3.0 mL) at 23° C. The resulting heterogeneous white mixture was stirred at 23° C. for 4 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-chloro-3-ethoxy-2-fluorophenyl)-5-fluoropicolinic acid as a white powder (140 mg, 88%): mp 163-165° C.; IR (thin film) 3486 (m), 3377 (s), 3155 (w), 2981 (w), 2935 (w), 1718 (s), 1614 (s) cm−1; 1H NMR (300 MHz, DMSO-d6) δ 7.45 (dd, J=9, 2 Hz, 1H), 7.28 (dd, J=9, 7 Hz, 1H), 7.01 (br s, 2H), 4.15 (q, J=7 Hz, 2H), 1.33 (t, J=7 Hz, 3H); ESIMS m/z 363 ([M+H]+).

후처리

  1. concentrationconcentrated via rotary evaporation
  2. filtrationvacuum filtered

출처 및 근거

ORD 기록
ord-b8c30e2460a4420682e04b9558372bb1
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169217B2

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