2-(Dimethoxymethyl)-1,8-naphthyridine → 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 1777851Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1>O=[Pt]=O.C(O)C>[CH3:15][O:14][CH:3]([O:2][CH3:1])[C:4]1[N:5]=[C:6]2[C:11]([CH2:10][CH2:9][CH2:8][NH:7]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

The procedure described in J. Org. Chem., 2004, 69 (6), pp 1959-1966 was used. Into a 5-l pressure tank reactor (5 atm) was placed 2-(dimethoxymethyl)-1,8-naphthyridine (intermediate 5, 200 g, 979 mmol), ethanol (3 l), PtO2 (12 g). The reactor was evacuated and flushed three times with nitrogen, followed by flushing with hydrogen. The mixture was stirred overnight at 23° C. under an atmosphere of hydrogen. This reaction was repeated four times. The solids were filtered out and the resulting mixture was concentrated under vacuum to give the title compound as a yellow solid.

Workup

customThe reactor was evacuated
customflushed three times with nitrogen
customby flushing with hydrogen
filtrationThe solids were filtered out
concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-4fe2d7741fb74394a96ef141f1e52c86
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266883B2

Reaction notes

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