Sodium Hydroxide → HCID 59510857, compound

HRID 1157068Notes

Reaction equation

HRID 1157068 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH3:13])[C:8](=[O:14])[C:7]=1[O:15][CH3:16])=[O:5])C.[OH-].[Na+]>CO>[CH3:16][O:15][C:7]1[C:8](=[O:14])[N:9]([CH3:13])[C:10]([CH3:12])=[CH:11][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59510851HCID 59510851, compound

Product 1

HCID 59510857HCID 59510857, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 16 (7.51 g, 33.3 mmol) in methanol (350 mL) was added a 4 M sodium hydroxide solution (350 mL). The resulting solution was heated at reflux, and after 2 h, methanol was removed under reduced pressure. An aqueous 3 N HCl solution was used to adjust the resulting solution to pH 1. The solution was extracted with ethyl acetate; the organic extracts were dried over sodium sulfate, and solvent was removed under reduced pressure to yield 6.44 g (98%) of 5 as a tan solid. 1H NMR (300 MHz, CD3OD): δ=2.40 (s, 3H, C—CH3), 3.58 (s, 3H, N—CH3), 3.86 (s, 3H, O—CH3), 6.36 (s, 1H, CH); 13C NMR (75 MHz, CD3OD): δ=20.6 (C—CH3), 32.6 (N—CH3), 61.0 (O—CH3), 105.9 (CH), 132.8, 143.4, 146.6, 162.6, 168.2; ESI-MS calcd for C9H11NO4 [M−H]−: 196.0610. found 196.0615.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux
  3. custommethanol was removed under reduced pressure
  4. extractionThe solution was extracted with ethyl acetate
  5. dry with materialthe organic extracts were dried over sodium sulfate, and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-f634ad4a4f2d4f758226062ca666d462
Source dataset
uspto-grants-2010_10
Patent number
US07807140B2

Reaction notes

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