2-Naphthol → HCID 136355259, compound

HRID 2109969Notes

Reaction equation

HRID 2109969 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([CH3:21])[CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18].[N:22]([O-])=O.[Na+].[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[OH:36].C(=O)([O-])[O-].[Na+].[Na+]>O.Cl.C(O)(C)C>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[OH:36][C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]=1[N:22]=[N:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([CH3:21])[CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 86632-NaphtholHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 86760853HCID 86760853, compound

Product 1

HCID 136355259HCID 136355259, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1.4 g (4.4 mmol) of the compound from Step 10.4 was dissolved in 20 mL of water and 1.5 g of hydrochloric acid (32%), the solution was cooled in an ice bath and to it was added over a period of 10 min 0.3 g (4.4 mmol) of sodium nitrite in 2 mL of water. The mixture was allowed to agitate for an additional 30 min after which a solution of 0.63 g (4.4 mmol) of 2-naphthol in 10 mL of isopropanol was added. The pH was adjusted to 8 to 9 by addition of saturated sodium carbonate solution which resulted in coupling with formation of a brown solution. After 1 hour, the solution was evaporated to dryness and, to isolate the pure dye, 80 mL of methanol was added to the residue. After an agitation period of 1 hour at room temperature, the inorganic salts were filtered off. The filtrate was concentrated to about 20% of its original volume and then 30 mL of isopropanol was added to induce crystallization. Cooling in an ice bath, filtration and drying at 40° C. under vacuum gave 1.6 g (67% of the original) of a red-brown product.

Workup

  1. additionwas added
  2. customresulted in coupling with formation of a brown solution
  3. customthe solution was evaporated to dryness
  4. customto isolate the pure dye, 80 mL of methanol
  5. additionwas added to the residue
  6. filtrationAfter an agitation period of 1 hour at room temperature, the inorganic salts were filtered off
  7. concentrationThe filtrate was concentrated to about 20% of its original volume
  8. addition30 mL of isopropanol was added
  9. customcrystallization
  10. temperatureCooling in an ice bath
  11. filtrationfiltration
  12. customdrying at 40° C. under vacuum
  13. customgave 1.6 g (67% of the original) of a red-brown product

Sources & evidence

ORD record
ord-7d91867b1e5a4d83a6b81bbf7044415f
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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