Nitronium tetrafluoroborate → 1-(Quinolin-2-yl)ethan-1-one

HRID 52545Notes

Reaction equation

HRID 52545 reaction equation
Br[C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8](C(C(OCC)=O)=O)[CH:7]([CH:19]([C:21](OC)=O)C)[CH2:6][CH2:5]2.F[B-](F)(F)F.[O:30]=[N+]=O.[N+]([O-])([O-])=O.[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.C(Cl)(Cl)Cl>[C:19]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[N:8]=1)(=[O:30])[CH3:21]

Participants

6

Reactant 3

HCID 11073463Nitronium tetrafluoroborateHCID 67722033HCID 67722033, compoundHCID 86750628Ammonium nitrate trifluoroacetic anhydride

Product 1

HCID 3187031-(Quinolin-2-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the route outlined in Example 22-6 to 7 starting with 6-bromo-N-ethoxalyl-2-(1-methoxycarbonylethyl)tetrahydroquinoline (less polar). In nitration step of Example 22-6, conditions of nitronium tetrafluoroborate in dichloromethane at room temperature were employed instead of those of refluxing ammonium nitrate-trifluoroacetic anhydride in chloroform: mp 242° C.; 1H NMR (270 MHz, DMSO-d6) δ12.08 (s, 1H), 7.21 (s, 1H), 7.17 (s, 1H), 4.93 (bd, 1H, J=10 Hz), 3.40 (s, 3H), 2.89 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.80 (dm, 1H, J=17.1 Hz), 2.60 (qd, 1H, J=7, 10 Hz), 2.23 (dm, 1H, J=13.5 Hz), 1.72~1.91 (m, 1H), 1.11 (d, 3H, J=7 Hz).

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-81352662ac1940d784a7a35e00bcef43
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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