Sodium Hydroxide → 5-((1,3-Benzodioxol-5-ylcarbonyl){4-[(4-butylphenyl)ethynyl]-benzyl}amino)-2-hydroxybenzoic acid

HRID 733554Notes

Reaction equation

HRID 733554 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:44]=[CH:43][C:16]([CH2:17][N:18]([C:30]3[CH:42]=[CH:41][C:33]4[O:34]C(C)(C)[O:36][C:37](=[O:38])[C:32]=4[CH:31]=3)[C:19]([C:21]3[CH:29]=[CH:28][C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CCO>[O:25]1[C:24]2[CH:28]=[CH:29][C:21]([C:19]([N:18]([CH2:17][C:16]3[CH:43]=[CH:44][C:13]([C:12]#[C:11][C:8]4[CH:9]=[CH:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=4)=[CH:14][CH:15]=3)[C:30]3[CH:42]=[CH:41][C:33]([OH:34])=[C:32]([CH:31]=3)[C:37]([OH:38])=[O:36])=[O:20])=[CH:22][C:23]=2[O:27][CH2:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841403N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-1,3-benzodioxole-5-carboxamide

Product 1

HCID 113648295-((1,3-Benzodioxol-5-ylcarbonyl){4-[(4-butylphenyl)ethynyl]-benzyl}amino)-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The titled compound was prepared following the procedure C using N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-1,3-benzodioxole-5-carboxamide and NaOH 5M aq. in the presence of EtOH as a pale yellow powder (55%). 1H NMR (CDCl3, 300 MHz) δ 10.47 (s, 1H), 7.44 (m, 5H), 7.26 (d, J=8.2 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H), 6.97 (m, 1H), 6.86 (m, 2H), 6.80 (d, J=9.1 Hz, 1H), 6.62 (d, J=8.6 Hz, 1H), 5.93 (s, 2H), 5.07 (s, 2H), 2.62 (t, J=7.8 Hz, 2H), 1.61 (m, 2H), 1.36 (m, 2H), 0.93 (t, J=7.2 Hz, 3H). M− (ESI): 546.2; M+ (ESI): 548: HPLC, Rt: 5.23 min (Purity: 98.3%)

Sources & evidence

ORD record
ord-539ca80b07df485ea7cb3f588e92c16f
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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