Sodium Bicarbonate → 2,5,6,7-Tetrahydro-1H-cyclopenta[c]pyridin-1-one

HRID 518584Notes

Reaction equation

Cl.[C:2]1(N)[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[OH:12][PH2]=O.N([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O.C(OCC)(=O)C>[C:2]1(=[O:12])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[CH:5]=[CH:4][NH:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound of step 4 (400 mg, 2.33 mmol) was dissolved in water (6.5 mL) and H3PO2 (2 mL, 50% w/w in water, 18.64 mmol) was added. The mixture was cooled to 0° C. and a solution of NaNO2 (180 mg 2.68 mmol) in water (6.5 mL) was added dropwise. The mixture was stirred at 0° C. for 1 h and then at room temperature overnight. The pH was adjusted to about 7 by careful addition of NaHCO3. Extractive work up using ethyl acetate gave the title compound (300 mg, 95%) as a yellow solid. 1H NMR (CDCl3, 300 MHz): δ 12.55 (s, 1H), 7.24 (d, J=6.3 Hz, 1H), 6.26 (d, J=6.3 Hz, 1H), 2.84-2.89 (m, 4H), 2.04-2.11 (m, 2H). LCMS: 136 (M+1)+

Workup

customat room temperature
customovernight

Sources & evidence

ORD record: ord-6fac01cc7d0f471aba99c4e2ba8d6e99
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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