Sodium Hydroxide → HCID 72953816, compound

HRID 2116838Notes

Reaction equation

HRID 2116838 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]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([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]1[CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86609835HCID 86609835, compound

Product 1

HCID 72953816HCID 72953816, compound

Procedure

In a manner similar to that of Example 1.g, by reaction of 193 mg (0.45 mmol) of methyl 4-[2-(3-tert-butyl4-pyrrolidin-1-ylphenyl)-2-hydroxyiminoethoxy]-2-hydroxybenzoate with 90 mg (2.3 mmol) of powdered sodium hydroxide. The final product is then recrystallized from a heptane/ethyl ether system. A beige-colored crystalline solid is obtained (m.p.=234° C., m=25 mg, yield=13%); (1H NMR (DMSO): 1.35 (s, 9H); 1.86 (s, 4H); 2.89 (s, 4H); 5.26 (s, 2H); 6.46-6.49 (d, J=8.6 Hz, 1H); 6.5 (s, 1 H); 7.40-7.42 (d, J=8.2 Hz, 1H); 7.49-7.51 (d, J=7.9 Hz, 1H); 7.66-7.68 (d, J=8.5 Hz, 2H); 11.9 (s, 1H)).

Workup

  1. customThe final product is then recrystallized from a heptane/ethyl ether system
  2. customA beige-colored crystalline solid is obtained (m.p.=234° C., m=25 mg, yield=13%)

Sources & evidence

ORD record
ord-824eaf080edb4cc6a2cb5641b276802d
Source dataset
uspto-grants-2008_10
Patent number
US07439396B2

Reaction notes

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