Calcium Carbonate → HCID 21502243, compound

HRID 1288471Notes

Reaction equation

HRID 1288471 reaction equation
N[C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[N:13]([O-:15])=[O:14].[Na+].N(O)=O.C(=O)([O-])[O-].[Ca+2]>S(=O)(=O)(O)O.O>[Cl:12][C:11]1[C:2]([N+:13]([O-:15])=[O:14])=[CH:3][CH:4]=[C:5]2[C:10]=1[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 10112Calcium CarbonateHCID 24529Nitrous AcidHCID 20523202HCID 20523202, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 21502243HCID 21502243, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

7-Amino-8-chloroisoquinoline (0.05 mole) in dilute aqueous sulfuric acid at 3° C. is treated with sodium nitrite (0.05 mole). After 30 minutes, the reaction mixture is tested for nitrous acid with starch/iodide paper as described in Example 15. When a positive reaction is obtained, the mixture is neutralized with aqueous calcium carbonate solution and added with stirring to a hot solution (50° C.) of 50 g. of sodium nitrite, 5 g. of cupric sulfate pentahydrate and 50 ml. of water containing 3 g. of cuprous oxide in suspension. The reaction mixture is heated to 70° C. for 10 minutes and then extracted with ether. The extract is evaporated to give 8-chloro-7-nitroisoquinoline. The product is purified by chromatography on silica gel, eluting with ether followed by recrystallization from methanol.

Workup

  1. customWhen a positive reaction
  2. customis obtained
  3. additionadded
  4. temperatureThe reaction mixture is heated to 70° C. for 10 minutes
  5. extractionextracted with ether
  6. customThe extract is evaporated

Sources & evidence

ORD record
ord-6e2b826d0c6a4e20a23e249663a98888
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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