Diethyl Ether → HCID 19771013, compound

HRID 1589827Notes

Reaction equation

HRID 1589827 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[C:14]([CH3:19])=[CH:15][CH:16]=[CH:17][CH:18]=1.C(OCC)C>O1CCOCC1>[ClH:1].[CH3:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7242O-ToluidineHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 19771013HCID 19771013, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Chloroisoquinoline (J. O. C. (1958), 23, 1071) (1.64 g, 0.01 mol) and o-toluidine (1.07 g, 0.01 mol) were heated together at reflux temperature in dry dioxan (20 ml) for 18 hours. After this time a light brown oil had precipitated in the hot solution. After cooling the mixture was evaporated to dryness to give an off-white, sticky solid. This was treated with diethyl ether (50 ml), collected, washed with ether and dried to give a white solid (2.07 g). This solid was crystallised from ethanol/ ether to give the title compound (1.97 g) as its hydrochloride salt, m.p. 229°-231°.

Workup

  1. customAfter this time a light brown oil had precipitated in the hot solution
  2. temperatureAfter cooling the mixture
  3. customwas evaporated to dryness
  4. customto give an off-white, sticky solid
  5. customcollected
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-e1b98bbd2b534fd68dd3d9105fbe05b2
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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