Hydrochloric Acid → 5,6-Dimethoxy-1H-indazol-3-amine

HRID 1414363Notes

Reaction equation

HRID 1414363 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.[N:15]([O-])=O.[Na+]>>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=2)[NH:1][N:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 7359672-Amino-4,5-dimethoxybenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 214091945,6-Dimethoxy-1H-indazol-3-amineYield 147.5%

Procedure

To a solution of 6-aminoveratronitrile (39 g, 0.2 mole) and conc. hydrochloric acid (329 ml) was added a solution of sodium nitrite (17 g, 0.25 mole in minimum amt. of water). The temperature was held below 0° during the addition. Keeping the temperature between 0° to 20° the resulting solution was added dropwise to stannous chloride (33.3 g, 1.76 mole) and conc. hydrochloric acid (153 ml). The precipitate was filtered and air dried overnight. The filter cake was placed in water (1100 ml), refluxed for 20-30 min and then filtered. The filtrate was cooled and then treated with sodium hydroxide (10% - 290 ml) to precipitate a tan solid. This solid was air dried at 60° to yield 57 g of 3-amino-5,6-dimethoxyindazole.

Workup

  1. additionThe temperature was held below 0° during the addition
  2. custombetween 0° to 20°
  3. filtrationThe precipitate was filtered
  4. customair dried overnight
  5. temperaturerefluxed for 20-30 min
  6. filtrationfiltered
  7. temperatureThe filtrate was cooled
  8. additiontreated with sodium hydroxide (10% - 290 ml)
  9. customto precipitate a tan solid
  10. customdried at 60°

Sources & evidence

ORD record
ord-4f9c33f65d844303b69c106fb2284651
Source dataset
uspto-grants-1977_01
Patent number
US04001269

Reaction notes

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