Sodium Hydroxide → HCID 178421970, compound

HRID 2205284Notes

Reaction equation

HRID 2205284 reaction equation
C([O-])(=O)C.[NH4+].C([NH:10][C:11]([C:13]1[C:18]([CH2:19][C:20](=O)[CH3:21])=[C:17]([CH3:23])[CH:16]=[CH:15][N:14]=1)=[O:12])(C)(C)C.[OH-].[Na+]>C(O)(=O)C>[CH3:23][C:17]1[C:18]2[C:13](=[C:11]([OH:12])[N:10]=[C:20]([CH3:21])[CH:19]=2)[N:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 117696310HCID 117696310, compound

Product 1

HCID 178421970HCID 178421970, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

Ammonium acetate (10.0 g, 130 mmol) followed by 4-methyl-3-(2-oxo-propyl)-pyridine-2-carboxylic acid tert-butylamide (1.61 g, 6.48 mmol) are added to acetic acid (20 mL) and the reaction mixture is heated at 110° C. for 3 h. The reaction mixture is cooled to RT and 20% NaOH is added until pH 6-7. The aqueous layer is extracted with DCM (3 times) and the combined organic layers are washed with brine, dried and evaporated under reduce pressure to furnish 4,6-dimethyl-[1,7]naphthyridin-8-ol (1.12 g, 99%) that is used as such.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. extractionThe aqueous layer is extracted with DCM (3 times)
  3. washthe combined organic layers are washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4db65f4c0b22495da64c0d2cf0dbb05a
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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