Sodium Hydroxide → HCID 59212472, compound

HRID 424710Notes

Reaction equation

HRID 424710 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([O:18]C)=[O:17])[C:3]1=[O:24].[OH-].[Na+]>CO.O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=2[CH3:23])[C:16]([OH:18])=[O:17])[C:3]1=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59212451HCID 59212451, compound

Product 1

HCID 59212472HCID 59212472, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylbenzoate 28 (3 g, 9 mmol) is suspended in a mixture of MeOH/water (1:1, mL) and treated with NaOH (2.2 g, 55 mmol) at 80° C. for 2 h. MeOH is removed in vacuo. The resultant mixture is acidified to pH=7, and the solid product is filtered and washed with water and dried overnight to yield 29. 1H NMR (400 MHz, DMSO-d6) δ 8.8 (s, 1H), 8.02 (s, 1H), 7.88 (dd, J=7.9, 1.8 Hz, 1H), 7.78 (d, J=1.7 Hz, 1H), 7.44 (s, 1H), 7.42 (d, J=8 Hz, 1H), 3.65 (s, 3H), 2.62 (s, 3H), 2.23 (s, 3H). LC/MS (M+1, m/z): 309.1.

Workup

  1. customMeOH is removed in vacuo
  2. filtrationthe solid product is filtered
  3. washwashed with water
  4. customdried overnight

Sources & evidence

ORD record
ord-b376b013dfec4d2a9faddb7443435225
Source dataset
uspto-grants-2012_01
Patent number
US08106068B2

Reaction notes

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