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Hydrochloric Acid → 5-((4-((4-Butylphenyl)ethynyl)benzyl)(hexyl)amino)-2-hydroxybenzoic acid

HRID 551891
ノート
印刷プレビュー

反応式

HRID 551891 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]3[CH:20]=[CH:21][C:22]([OH:29])=[C:23]([CH:28]=3)[C:24]([O:26]C)=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]3[CH:20]=[CH:21][C:22]([OH:29])=[C:23]([CH:28]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11562363Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate

生成物 1

HCID 114972825-((4-((4-Butylphenyl)ethynyl)benzyl)(hexyl)amino)-2-hydroxybenzoic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 962
Water
溶媒

実験手順

To a solution of methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate in MeOH (400 mL) and water (40 mL) was added an aqueous solution of NaOH (6.0 mL, 5N). The reaction mixture was sired at 60° C. overnight. Then an aqueous solution of HCl (10 mL, 5N) was added and the solvents were removed under reduced pressure. The residue was taken up in water and extracted with Et2O (3×). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure to give a yellow solid. Precipitation from a DCM/MeOH mixture gave 2.17 g (53%, stop e and f) of the title compound as a beige powder. HPLC, Rt: 4.8 min purity: 99.7%). LC/MS, M+(ESI): 484.4, M−(ESI): 482.2. 1H NMR (CDCl3/CD3OD (15/1)) δ: 7.39 (m, 4H), 7.18-7.09 (m, 5H), 6.87 (dd, J=9.0, 3.0 Hz, 11), 6.78 (d, J=9.0 Hz, 1H), 4.38 (s, 2H), 3.22 (t, J=7.5 Hz, 2H), 2.57 (t, J=7.8 Hz, 2H), 1.55 (m, 4H), 1.34-1.21 (m, 8H), 0.90-0.75 (m, 6H).

後処理

  1. customthe solvents were removed under reduced pressure
  2. extractionextracted with Et2O (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customto give a yellow solid
  6. customPrecipitation from a DCM/MeOH mixture

出典と根拠

ORDレコード
ord-d4a88a61a5de431fb5357613fe1c6291
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947851B2

反応ノート

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