Lithium Hydroxide → 2'-Methyl-2-nitro-[1,1'-biphenyl]-4-carboxylic acid

HRID 219777

반응식

HRID 219777 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 59606541Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 594958102'-Methyl-2-nitro-[1,1'-biphenyl]-4-carboxylic acid수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Methyl 2′-methyl-2-nitro-1,1′-biphenyl-4-carboxylate, prepared in step 1 (2.5 g, 9.2 mmol) was dissolved in dry THF (20 mL) and cooled to 0° C. To this solution was added lithium hydroxide (1.15 g, 27.6 mmol) in water (5 mL) and the mixture was stirred at RT for 4 h. The solvents were concentrated and the aqueous residue was washed with EtOAc. The aqueous layer was separated and acidified with 1.5N HCl to pH 2-3 and extracted with DCM. DCM was washed with water and dried over sodium sulphate and evaporated under reduced pressure to obtain the title compound as a yellow solid (1.6 g, 70%). 1H NMR: (DMSO-d6, 400 MHz) δ 13.67 (bs, 1H), 8.49 (s, 1H), 8.26-8.24 (d, 1H), 7.58-7.56 (m, 1H), 7.35-7.32 (m, 2H), 7.27-7.12 (d, 1H), 7.10 (d, 1H), 2.09-1.99 (s, 3H). LC/MS (Method A): 255.9 (M−H)−. HPLC (Method B) Rt 1.79 min (Purity: 99.16%).

후처리

  1. concentrationThe solvents were concentrated
  2. washthe aqueous residue was washed with EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM
  5. washDCM was washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-38cbc011b8724d5397bc3d2590a7ad68
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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