Sodium Hydroxide → HCID 72816966, compound

HRID 2116836Notes

Reaction equation

HRID 2116836 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[N:30][OH:31])[CH2:17][O:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>>[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[N:30][OH:31])[CH2:17][O:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86609833HCID 86609833, compound

Product 1

HCID 72816966HCID 72816966, compound

Procedure

In a manner similar to that of Example 1.g, by reaction of 120 mg (0.3 mmol) of methyl 4-[2-(3-tert-butyl-4-diethylaminophenyl)-2-hydroxyiminoethoxy]-2-hydroxybenzoate with 46 mg (1.4 mmol) of powdered sodium hydroxide. The final product is then recrystallized from a heptane/ethyl ether system. A white crystalline solid is obtained (m.p.=210° C., m=60 mg, yield=48%); (1H NMR (DMSO): 0.96-1.00 (t, 6H); 1.38 (s, 9H); 2.7-3 (m, 4H); 5.26 (s, 2H); 6.46-6.49 (dd, J=6.4 Hz, J′=2.4 Hz, 1H); 6.55 (d, J=2.4 Hz, 1H); 7.26-7.28 (d, J=8.3 Hz, 1H); 7.46-7.48 (dd, J=6.2 Hz, J′=2.03 Hz,1H); 7.65-7.67 (d, J=8.8 Hz, 1H); 7.69 (d, J=2.03 Hz, 1H); 11.9 (s, 1H); 13-14 (s, 1H)).

Workup

  1. customThe final product is then recrystallized from a heptane/ethyl ether system
  2. customA white crystalline solid is obtained (m.p.=210° C., m=60 mg, yield=48%)

Sources & evidence

ORD record
ord-6065a9a9afbd4cd6a3ccc03e795047f2
Source dataset
uspto-grants-2008_10
Patent number
US07439396B2

Reaction notes

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