Hydrochloric Acid → 3-Amino-5-phenylpicolinic acid

HRID 69939

반응식

HRID 69939 반응식
[N+:1]([C:4]1C(C#N)=[N:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O.[Sn](Cl)Cl.Cl.[C:22]([O:25]CC)(=[O:24])[CH3:23]>CN(C=O)C.C(N(CC)CC)C>[NH2:1][C:4]1[C:23]([C:22]([OH:25])=[O:24])=[N:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 463147453-Nitro-5-phenylpicolinonitrile

생성물 1

HCID 690441223-Amino-5-phenylpicolinic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 3-nitro-5-phenylpicolinonitrile (1 eq) in 10 mL of DMF was added tin (II) chloride dehydrate (7.0 eq) at room temperature. The reaction mixture was stirred at that temperature overnight. The mixture was diluted with 150 mL of ethyl acetate and 30 mL of triethyl amine. After filtration, the filtrate was concentrated under reduced pressure to give a solid, which was added 2 mL of concentrated HCl. The mixture was stirred in microwave at 90° C. for 10 minutes. After standing over night, the solid was collected by filtration, which was dissolved in 10 mL of 1N NaOH. The resulting mixture was extracted with 50 mL of ethyl acetate. The aqueous layer was acidified by 1 N HCl to pH 7.0 to yield 3-amino-5-phenylpicolinic acid, which was collected by filtration. LC/MS (m/z): 215.1 (MH+).

후처리

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a solid, which
  4. stirringThe mixture was stirred in microwave at 90° C. for 10 minutes
  5. waitAfter standing over night
  6. filtrationthe solid was collected by filtration, which
  7. dissolutionwas dissolved in 10 mL of 1N NaOH
  8. extractionThe resulting mixture was extracted with 50 mL of ethyl acetate

출처 및 근거

ORD 기록
ord-636abf1bf85942ff961bf0acc5cc0bc6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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