Potassium Nitrate → HCID 58124932, compound

HRID 1971652Notes

Reaction equation

HRID 1971652 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8][N:7]=1)=[O:5])[CH3:2].[N+:18]([O-])([O-:20])=[O:19].[K+].C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH3:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=2)[CH2:9][CH2:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 516892Sodium BicarbonateHCID 23128313HCID 23128313, compound

Product 1

HCID 58124932HCID 58124932, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 35 g of 6-methoxy-3,4-dihydroisoquinoline-1-carboxylic acid ethyl ester in 250 ml of concentrated sulphuric acid was added, at 0° C., 21 g of KNO3 in portions over 5 min. The reaction mixture was stirred for 1 h and then poured with stirring onto 500 g of NaHCO3. The resulting mixture was diluted with 2 l of ice-water and the product was extracted into dichloromethane. The organic layer was washed with water, dried, concentrated and the residue was treated with diethyl ether, to provide 34 g of 6-methoxy-7-nitro-3,4-dihydroisoquinoline-1-carboxylic acid ethyl ester, 5d MS-ESI: [M+1] 279.07. NMR (CDCl3) δ 1.42 (t, 3, OCH2CH3), 2.82 (t, 2, CH2), 3.94 (t, 2, CH2), 4.46 (q, 2, OCH2CH3), 6.92 and 8.44 (2×s, 2, Ar—H).

Workup

  1. additionpoured
  2. extractionthe product was extracted into dichloromethane
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionthe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-66cf606891e14d1dacd50f837ee2a5f7
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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