Sodium Hydroxide → 5-[{4-[(4-Butylphenyl)ethynyl]benzyl}(2-naphthoyl)amino]-2-hydroxybenzoic acid

HRID 733562Notes

Reaction equation

HRID 733562 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][N:18]([C:31]3[CH:43]=[CH:42][C:34]4[O:35]C(C)(C)[O:37][C:38](=[O:39])[C:33]=4[CH:32]=3)[C:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=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>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][N:18]([C:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[O:20])[C:31]3[CH:43]=[CH:42][C:34]([OH:35])=[C:33]([CH:32]=3)[C:38]([OH:39])=[O:37])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841390N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-2-naphthamide

Product 1

HCID 114442675-[{4-[(4-Butylphenyl)ethynyl]benzyl}(2-naphthoyl)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)-2-naphthamide and NaOH 5M aq. in the presence of EtOH as a white powder (51%). 1H NMR (CDCl3/MeOD 35:1, 300 MHz) δ 7.92 (s, 1H), 7.73 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 1H), 7.54 (s, 1H), 7.45 (m, 6H), 7.32 (m, 3H), 7.16 (d, J=7.9 Hz, 2H), 6.94 (d, J=8.3 Hz, 1H), 6.68 (d, J=8.6 Hz, 1H), 5.13 (s, 2H), 2.62 (t, J=7.7 Hz, 2H), 1.60 (m, 2H), 1.35 (m, 2H), 0.93 (t, J=7.2 Hz, 3H). M− (ESI): 552.3; M+ (ESI): 554.2. HPLC, Rt: 5.53 min (Purity: 98.9%).

Sources & evidence

ORD record
ord-74502a2229e3405a805a197f514dd0c2
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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