Anthranilic Acid → HCID 70513723, compound

HRID 1463073Notes

Reaction equation

HRID 1463073 reaction equation
[C:1]1([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH3:9].[OH-].[K+].C(O)(=O)C1C(=CC=CC=1)[NH2:29].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>CO.O>[NH2:29][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([OH:23])=[C:13]([C:11](=[O:12])[NH:10][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[O:7][CH2:8][CH3:9])[CH:22]=1

Participants

8

Reactant 5

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 24489Sodium DithioniteHCID 70515526HCID 70515526, compound

Product 1

HCID 70513723HCID 70513723, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11.64 g (0.04 mol) of 2-(N-2-phenetylcarbamoyl)-1-naphthol was dissolved in a mixture composed of 12 g of potassium hydroxide, 25 ml of water and 200 ml of methanol. To the resulted solution, an aqueous solution of diazonium salt prepared with using 5.75 g of anthranilic acid was added to 0° to 5° C. After stirred at 5° to 10° C. for 30 minutes, 100 ml of a 20% aqueous solution of potassium hydroxide was added thereto and 50 g of sodium hydrosulfite was added at 50° to 60° C. After stirring at the same temperature for 10 minutes, it was cooled with ice and neutralized with diluted hydrochloric acid. The formed light yellow precipitate was filtered off.

Workup

  1. additionwas added to 0° to 5° C
  2. stirringAfter stirring at the same temperature for 10 minutes
  3. filtrationThe formed light yellow precipitate was filtered off

Sources & evidence

ORD record
ord-cc5cf8ac6d9c4322a7ee200938decedc
Source dataset
uspto-grants-1984_07
Patent number
US04463079

Reaction notes

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