Isopropanol → HCID 68771727, compound

HRID 1042296Notes

Reaction equation

HRID 1042296 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.FC(F)(F)C(O)=O.C(O)(C)C>C(Cl)(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH:25][C:2]2[C:11]3[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH3:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6422Trifluoroacetic acidHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amineHCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

Product 1

HCID 68771727HCID 68771727, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A glass microwave reaction vessel was charged with 1-chloro-6-methyl-5-nitroisoquinoline (0.22 g, 1.0 mmol), (R)-1-(4-chlorophenyl)ethanamine (0.31 g, 2.0 mmol), 2,2,2-trifluoroacetic acid (0.011 g, 0.10 mmol) and isopropanol (1 mL). The reaction mixture was stirred and heated in a microwave reactor at 140° C. for 60 min. The reaction mixture was diluted with chloroform, washed with 10% sodium carbonate, dried over sodium sulfate and concentrated. The crude product was chromatographed on silica gel eluting with 20% ethyl acetate/hexane to give (R)-N-(1-(4-chlorophenyl)ethyl)-6-methyl-5-nitroisoquinolin-1-amine as a solid. MS Found: (ESI pos. ion) m/z 342 (M+H+).

Workup

  1. customA glass microwave reaction vessel
  2. washwashed with 10% sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-37fa9fcbe45c44f2ad01b7ca313e94c4
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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