Hydrochloric Acid → HCID 22261534, compound

HRID 1610193Notes

Reaction equation

HRID 1610193 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13].N([O-])=O.[Na+].[ClH:21]>O.[Cu]Cl>[Cl:21][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 22261675Ethyl 5-aminonaphthalene-1-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22261534HCID 22261534, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

While stirring ethyl 5-amino-1-naphthoate (1.358 g, 6.309 mmol) in conc. hydrochloric acid (10 ml), a solution of sodium nitrite (0.52 g, 7.57 mmol) in water (1 ml) was added dropwise under ice-cooling and the mixture was stirred at said temperature for 0.5 hr. To the reaction solution was added a solution of copper(I) chloride (0.34 g, 3.47 mmol) in conc. hydrochloric acid (2 ml) under ice-cooling, and the mixture. was stirred at 100° C. for 0.5 hr. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. customfor 0.5 hr
  3. temperaturecooling
  4. stirringwas stirred at 100° C. for 0.5 hr
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained crude product
  9. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1)
  10. customto give the objective substance

Sources & evidence

ORD record
ord-a042fc2eea494b2085c5fe99a0dbb0eb
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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