6,7-Dihydro-5H-1-pyridin-5-one → (5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

Reaction equation

O1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[N:11]/[OH:12])/[CH2:3]C1.[N:13]1C=CC=C2C(=O)CCC=12>>[N:13]1[CH:8]=[CH:7][CH:6]=[C:5]2/[C:4](=[N:11]\[OH:12])/[CH2:3][CH2:9][C:10]=12

Participants

Reactant 2

HCID 15125216,7-Dihydro-5H-1-pyridin-5-one

HCID 9673039Chroman-4-one oxime

Product 1

HCID 45079548(5Z)-N-Hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-5-imine

Procedure

Following the procedure for the preparation of (4E)-2,3-dihydro-4H-chromen-4-one oxime but substituting 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, DMSO-d6) δ) 11.11, 8.50, 7.89, 7.27, 3.04, 2.81; HRMS (EI) calcd for C8H8N2O 148.0637, found 148.0628.

Sources & evidence

ORD record: ord-e0a5635100d149c6ab88c7513bd23082
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041672B2

Reaction notes

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