tert-Butyl 3-nitro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate → 1,6-Naphthyridin-3-amine

HRID 888092Notes

Reaction equation

C(OC([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[CH:13][C:12]([N+:18]([O-])=O)=[CH:11][C:10]=2[CH2:9]1)=O)(C)(C)C>CCO.[Pd]>[N:14]1[C:15]2[C:10](=[CH:9][N:8]=[CH:17][CH:16]=2)[CH:11]=[C:12]([NH2:18])[CH:13]=1

Participants

Conditions

Temperature: 170 °C

Procedure

3-Nitro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (1.0 g, 3.6 mmol), was added to EtOH (10 mL) in a sealed tube. 10% Pd/C (500 mg) was added and the mixture was heated to 170° C. for 16 h. The reaction mixture was cooled to RT, diluted with EtOH (10 mL), and filtered through Celite®. The solvent was removed under reduced pressure affording [1,6]naphthyridin-3-ylamine as yellow solid.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered through Celite®
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2e94d4a935744b2ea81491839909ac10
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247556B2

Reaction notes

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