Sulfuric Acid → HCID 13491592, compound

HRID 1284917Notes

Reaction equation

HRID 1284917 reaction equation
[CH3:1][N:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[C:5]([NH:18][C:19](=[O:23])[CH:20]=NO)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[OH:24]S(O)(=O)=O.[OH-].[Na+]>>[CH3:1][N:2]1[CH2:11][CH:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]2=[CH:8][CH:7]=[C:6]3[C:5]([NH:18][C:19](=[O:23])[C:20]3=[O:24])=[C:4]2[CH2:3]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 86740595HCID 86740595, compound

Product 1

HCID 13491592HCID 13491592, compound

Conditions

Temperature
45 °C

Procedure

17.5 g (0.0566 mol) of N-methyl-4-phenyl-8-(hydroxyiminoacetylamino)isoquinoline were added in small portions to 43.75 ml of concentrated H2SO4 at 45° C. and the mixture was warmed at 45° C. for 75 minutes. It was cooled to room temperature and poured onto 450 g of ice. A pH of 6.8 was then established with 2N NaOH. The precipitate which had separated out was filtered off with suction and washed with water. After drying, 15.3 g (92.5% of theory) of orange-colored crude product are obtained. (Melting point of the pure product=about 188° C., decomposition).

Workup

  1. temperatureIt was cooled to room temperature
  2. customThe precipitate which had separated out
  3. filtrationwas filtered off with suction
  4. washwashed with water
  5. customAfter drying
  6. custom15.3 g (92.5% of theory) of orange-colored crude product are obtained

Sources & evidence

ORD record
ord-9ec75fc4439343be883e2b3cde9001f6
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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