Ammonia → HCID 67404437, compound

HRID 333680Notes

Reaction equation

HRID 333680 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1.[NH3:25]>C(O)C>[NH2:25][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53379476HCID 53379476, compound

Product 1

HCID 67404437HCID 67404437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 25-mL Schlenk flask, under argon, 1-chloro-7-methoxy-3-(4-methoxyphenyl)-4-nitroisoquinoline (100 mg, 0.43 mmol) is dissolved in 20 mL of a saturated solution of ammonia in ethanol. After stirring for 4 days at 80° C., the medium is concentrated under vacuum then purified by silica gel column chromatography with dichloromethane-ethanol (95/5) as eluent in order to produce the expected amine compound 71 (79 mg, 56%) in the form of a yellow solid. 1H NMR CDCl3 δ 7.81 (d, 1H), 7.60 (d, 2H), 7.45 (d, 1H), 7.07 (s, 1H), 6.99 (d, 2H), 5.44 (s, 2H), 3.99 (s, 3H), 3.87 (s, 3H); MS 326 [M+H]+.

Workup

  1. concentrationthe medium is concentrated under vacuum
  2. customthen purified by silica gel column chromatography with dichloromethane-ethanol (95/5) as eluent in order

Sources & evidence

ORD record
ord-5a500c683890452b9c65dd5fa40d0f8e
Source dataset
uspto-grants-2014_11
Patent number
US08883763B2

Reaction notes

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