Hydrochloric Acid → 7-Methoxy-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1943150Notes

Reaction equation

CC(C)(C)C([NH:5][C:6]1[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17]CCC)=O)=[CH:10][CH:9]=[C:8]([O:21]C)[N:7]=1)=O.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:17][O:16][C:14]1[N:5]=[C:6]2[C:11]([CH2:10][CH2:9][C:8](=[O:21])[NH:7]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of butyl 3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]propanoate (86.01 g, 256 mmol) in hydrochloric acid (500 ml, 3000 mmol) (6M aqueous), was heated at 80° C. for 6 h. Reaction was cooled, treated with water (500 ml), transferred to a 5 L conical flask and carefully neutralised with solid potassium carbonate (requires around 250 g) (much effervescence was observed). The mixture was then extracted with 20% MeOH/DCM (3×500 ml). The combined organic solvents were then dried (MgSO4), filtered and evaporated to give the crude product as a yellow solid (35.84 g, 79%).

Workup

customReaction
temperaturewas cooled
customtransferred to a 5 L conical flask
extractionThe mixture was then extracted with 20% MeOH/DCM (3×500 ml)
dry with materialThe combined organic solvents were then dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-bae29e92a4bc40e09383e407b8461bc6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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