Sodium Hydroxide → Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate

HRID 551890Notes

Reaction equation

HRID 551890 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:19]3[CH:31]=[CH:30][C:22]4[O:23][C:24](C)(C)[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:19]3[CH:31]=[CH:30][C:22]([OH:23])=[C:21]([CH:20]=3)[C:26]([O:25][CH3:24])=[O:27])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 575545156-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 11562363Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (4.41 g, 8.4 mmol) in MeOH (500 mL) and water (30 mL) was added an aqueous solution of NaOH (7.0 mL, 5N). The reaction mixture was stirred at rt for 2 hrs and a yellow powder precipitated out progressively. Filtration and washing with water (2×) gave the title compound as a yellow powder. HPLC, Rt: 5.3 min (purity: 98.7%). LC/MS, M+(ESI): 498.3. 1H NMR (CDCl3) δ: 10.16 (s, 1H), 7.45 (m, 4H), 7.19 (m, 5H), 6.94 (dd, J=9.0, 3.0 Hz, 1H), 6.86 (d, J=9.0 Hz, 1H), 4.43 (s, 2H), 3.92 (s, 3H), 3.28 (t, J=7.5 Hz, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.60 (m, 4H), 1.30 (m, 8H), 0.92 (m, 6H).

Workup

  1. customa yellow powder precipitated out progressively
  2. filtrationFiltration
  3. washwashing with water (2×)

Sources & evidence

ORD record
ord-f060ebc6b6b7447f87fbd48a917b69c7
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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