Sodium Bicarbonate → 2,3-Dimethoxy-6-(5-nitroisoquinolin-4-yl)phenol

HRID 895400Notes

Reaction equation

HRID 895400 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:24]COC)=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[N+:21]([O-:23])=[O:22])[CH:14]=[N:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[N+:21]([O-:23])=[O:22])[CH:14]=[N:13][CH:12]=2)[C:4]=1[OH:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 129719194-(3,4-Dimethoxy-2-methoxymethoxyphenyl)-5-nitroisoquinoline

Product 1

HCID 129719202,3-Dimethoxy-6-(5-nitroisoquinolin-4-yl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After dissolving isoquinoline 4a (5.285 g, 0.014 mol) in 200 ml of methanol by gentle heating, p-toluenesulfonic acid monohydrate (8.15 g; 0.043 mol) was added in several portions. Stirring was continued for four hours at room temperature. After completion of the reaction, the solution was made basic by adding saturated sodium bicarbonate. The product was then extracted with dichlormethane (3×250 ml), dried (Na2SO4), and concentrated. The resulting yellow solid (4.65 g; 98%) was used directly in the next reaction. An analytical sample was recrystallized from methanol: mp 170-174° C.; 1H NMR: (300 MHz, CDCl3): 9.33 (s, 1H); 8.62 (s, 1H); 8.24 (dd, 1H, J=7.2, 0.9 Hz); 7.99 (dd, 1H, J=6.3, 1.2 Hz); 7.67 (t, 1H, J=7.8 Hz); 6.96 (d, 1H, J=8.7 Hz); 6.59 (d, 1H, J=8.7 Hz); 5.88 (bs, 1H); 3.94 (s, 3H); 3.92 (s, 3H). CIMS m/z: 327 (M+H+, 100%). Anal Calc'd for C17H14N2O5: C, 62.57; H, 4.32; N, 8.58. Found: C, 62.18; H, 4.38; N, 8.35.

Workup

  1. additionwas added in several portions
  2. customAfter completion of the reaction
  3. extractionThe product was then extracted with dichlormethane (3×250 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting yellow solid (4.65 g; 98%) was used directly in the next reaction
  7. customAn analytical sample was recrystallized from methanol

Sources & evidence

ORD record
ord-5541295628424500acc35a4dffcc276d
Source dataset
uspto-grants-2005_07
Patent number
US06916823B2

Reaction notes

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