Hydrochloric Acid → HCID 178435359, compound

HRID 487407Notes

Reaction equation

[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](SC1C=CC=CC=1)=[CH:6][C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:32]=2)=[CH:18][CH:17]=1)[CH3:2].[Na].[ClH:61]>CO>[ClH:61].[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:29][N:30]=[N:31][N:32]=2)=[CH:20][CH:21]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5,7-Diethyl-1-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one (A) (5.0 g) was added to a solution of sodium (2.05 g) in methanol (100 ml) and the solution was heated at reflux for 16 hours under an atmosphere of argon. The mixture was cooled to 0° C. and acidified with concentrated hydrochloric acid (20 ml). The precipitated solid was collected by filtration and recrystallised successively from isopropanol (60 ml), water (30 ml) and ethanol (10 ml) to give 5,7-diethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2,3,4-tetrahydro-1,6-naphthyridin-2-one hydrochloride (2.36 g), m.p. 260°-263° C. (decomposition); microanalysis, found: C, 65.6; H, 5.9; N, 17.8%; C26H26N6O.HCl requires: C, 65.7; H, 5.7; N, 17.7.

Workup

temperaturethe solution was heated
temperatureat reflux for 16 hours under an atmosphere of argon
filtrationThe precipitated solid was collected by filtration
customrecrystallised successively from isopropanol (60 ml), water (30 ml) and ethanol (10 ml)

Sources & evidence

ORD record: ord-e0ca8ca0e6cb4a789e93e1b80b968c94
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294620

Reaction notes

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