Methanol → HCID 178515136, compound

HRID 323614Notes

Reaction equation

HRID 323614 reaction equation
[NH:1]([N:8]1[C:20](=[O:21])[C:19]2[C:18](=[O:22])[C:17]3[CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>CS(O)(=O)=O>[OH:26][C:9]1[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[CH:16][C:17]=3[C:18](=[O:22])[C:19]=2[C:20](=[O:21])[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 219976732-Anilino-7-nitro-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1,3,9-trione

Product 1

HCID 178515136HCID 178515136, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

2-Anilino-7-nitro-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1,3,9-trione (0.830 g, 2.37 mM) was dissolved with stirring in methanesulfonic acid (42 mL) to give a deep orange solution. Methanol (420 mL) was added and the resulting yellow solution heated to reflux for 2 hours to give a yellow suspension. Heat was removed and the suspension was stirred at room temperature for 3 hours. The solids were removed by filtration, and the filtrate was allowed to stand for 20 hours. More solids formed in the filtrate during this time, and the suspension was refiltered. This filtrate was then concentrated to about 250 mL and diluted with water (400 mL) to give a yellow precipitate. These solids were collected and washed with aqueous methanol (50%) and then ether to give the title compound (0.590 g, 71%) as a yellow powder, mp 382-385° C.; MS(CI): 351 (M+H).

Workup

  1. customto give a deep orange solution
  2. temperaturethe resulting yellow solution heated
  3. temperatureto reflux for 2 hours
  4. customto give a yellow suspension
  5. temperatureHeat
  6. customwas removed
  7. customThe solids were removed by filtration
  8. waitto stand for 20 hours
  9. customMore solids formed in the filtrate during this time
  10. concentrationThis filtrate was then concentrated to about 250 mL
  11. additiondiluted with water (400 mL)
  12. customto give a yellow precipitate
  13. customThese solids were collected
  14. washwashed with aqueous methanol (50%)

Sources & evidence

ORD record
ord-8b2d871bbc3241f4971563e8f1556617
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

Loading…