Phosphorus oxychloride → HCID 178478306, compound

HRID 1919691Notes

Reaction equation

HRID 1919691 reaction equation
[N:1]1[N:2]=[C:3]([C:6]2[C:11]3[NH:12][C:13](=O)[C:14]4[C:19]([C:10]=3[CH:9]=[CH:8][CH:7]=2)=[CH:18][N:17]=[CH:16][CH:15]=4)[NH:4][CH:5]=1.P(Cl)(Cl)([Cl:23])=O>C(#N)C>[Cl:23][C:13]1[C:14]2[C:19](=[CH:18][N:17]=[CH:16][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:3]3[NH:4][CH:5]=[N:1][N:2]=3)[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518577HCID 178518577, compound

Product 1

HCID 178478306HCID 178478306, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen atmosphere, 7-(4H-1,2,4-triazol-3-yl)benzo[c][2,6]naphthyridin-5(6H)-one (1.8 g, 6.84 mmol) was mixed with Phosphorus oxychloride (3.2 ml) in acetonitrile (20 ml). The mixture was stirred overnight at 100° C. The volatiles were removed in vacuo. The resulting solid was suspended in CH2Cl2 and a little bit of MeOH. After filtration and drying, crude 5-chloro-7-(4H-1,2,4-triazol-3-yl)benzo[c][2,6]naphthyridine (2.04 g) was isolated as a greenish solid. LCMS (ES) m/z 282 [M+1]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. filtrationAfter filtration
  3. customdrying

Sources & evidence

ORD record
ord-e5a8736bd97a44e2b2f0d43ba58f0a10
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…