Phenolphthalein → alpha-(2-Fluoro-4-methylphenylamino)isovaleric acid

HRID 648254노트

반응식

HRID 648254 반응식
Br[CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].C1C=C2C(OC(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)C2=CC=1)=O.C[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].[F:42][C:43]1[CH:49]=[C:48]([CH3:50])[CH:47]=[CH:46][C:44]=1[NH2:45].[OH-].[Na+].CCOCC>CO.CN(P(N(C)C)(N(C)C)=O)C>[F:42][C:43]1[CH:49]=[C:48]([CH3:50])[CH:47]=[CH:46][C:44]=1[NH:45][CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4]

참가 물질

9

반응물 6

HCID 4764PhenolphthaleinHCID 112682-Bromoisovaleric acidHCID 11430Potassium CarbonateHCID 679842-Fluoro-4-methylanilineHCID 10942334Sodium MethoxideHCID 86719931NaOH ether

생성물 1

HCID 20482718alpha-(2-Fluoro-4-methylphenylamino)isovaleric acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 12679Hexamethylphosphoramide용매

실험 절차

A solution of α-bromoisovaleric acid (8.17 mmole) in methanol is titrated to the phenophthalein end point using sodium methoxide. The solvent is removed by rotoevaporation and then there is added potassium carbonate (1.69 g), 2-fluoro-4-methylaniline (16.38 mmole) and 3 ml HMPT. The reaction is heated at 60° for about 5 hours and then worked up with 5% sodium hydroxide/ether and washed with water (3×). The basic layer is acidified and extracted with ether, washed with water and brine, dried over sodium sulfate and rotoevaporated to yield α-(2-fluoro-4-methylphenylamino)isovaleric acid. (2-Fluoro-4-methylaniline is prepared from 3-fluoro-4-nitrotoluene in a Parr bottle using platinum oxide and hydrogen in ethanol.)

후처리

  1. customThe solvent is removed by rotoevaporation
  2. temperatureThe reaction is heated at 60° for about 5 hours
  3. washwashed with water (3×)
  4. extractionextracted with ether
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-b00407b544244c2b81d8fcdf8b143daa
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04411912

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