4-Methylbenzaldehyde → 6-Methylisoquinolin-5-amine

HRID 1418030Notes

Reaction equation

HRID 1418030 reaction equation
CC1C=CC(C=O)=CC=1.[CH3:10][C:11]1[C:12]([N+:21]([O-])=O)=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[N:16][CH:15]=[CH:14]2.[Sn](Cl)(Cl)(Cl)Cl>C(O)(=O)C.Cl>[NH2:21][C:12]1[C:11]([CH3:10])=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 24287Tin tetrachlorideHCID 250590506-Methyl-5-nitroisoquinoline2×

Product 1

HCID 397336986-Methylisoquinolin-5-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

By carrying out the preparation according to Stages 1 and 2 of PREPARATION IX above and by using 4-methylbenzaldehyde as starting reactant, 6-methyl-5-nitroisoquinoline is prepared. 4.0 g of 6-methyl-5-nitroisoquinoline are dissolved in a solution of 80 ml of acetic acid and 40 ml of concentrated hydrochloric acid, 40.0 g of tin chloride are then added and the reaction mixture is heated at reflux for 3 hours and then left for 12 hours at room temperature. The crystals formed are filtered off, taken up in water and basified with 10N sodium hydroxide. The extraction is carried out with dichloromethane and the organic phase is dried and evaporated to dryness to obtain 0.52 g of yellow crystals. 1H NMR (CDCl3): 2.37 (s, 3H, --CH3), 4.18 (broad s exchangeable with D2O, 2H, --NH2), 7.29 (d, J=8.8, 1H, H7), 7.44 (d, J=8.8, 1H, H4), 7.53 (d, J=6.2, 1H, H8), 8.49 (d, J=5.8, 1H, H3), 9.13 (s, 1H, H1).

Workup

  1. customis prepared
  2. additionare then added
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 3 hours
  5. customThe crystals formed
  6. filtrationare filtered off
  7. extractionThe extraction
  8. customthe organic phase is dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-edcf6149238b46239ade4ad91f4e26ae
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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