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

HRID 219777

反応式

HRID 219777 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-38cbc011b8724d5397bc3d2590a7ad68
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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