Hydrochloric Acid → HCID 18421080, compound

HRID 990312Notes

Reaction equation

HRID 990312 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:15](=[O:18])([O-])[O-:16].[Na+].[Na+].ClC(OC[CH:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=O.Cl>O.O1CCOCC1>[CH:28]1[C:27]2[CH:26]([O:16][C:15]([NH:1][C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9]4)=[CH:4][CH:3]=3)=[O:18])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 220418337-Amino-2-naphthoic acid

Product 1

HCID 18421080HCID 18421080, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To 0.504 g (2.70 mmol) of 7-aminonaphthalene-2-carboxylic acid (106; prepared according to the procedure in Harrison, H. A. and Royle, F. A. J. Chem. Soc., 1926, 84) was added 10 mL of dioxane, 5 mL of 10% sodium carbonate, and 35 mL of water. To this clear solution was added 0.786 g (2.97 mmol) of 9-fluorenylmethyl chloroformate, portionwise, over 15 minutes. After 3 hours, the reaction was acidified with 1N HCl and the resulting white precipitate was collected by vacuum filtration. This solid was suspended in diethyl ether and stirred to give a fine precipitate that was collected by vacuum filtration. This provided 0.948 g of compound 107.

Workup

  1. customprepared
  2. waitAfter 3 hours
  3. filtrationthe resulting white precipitate was collected by vacuum filtration
  4. customto give a fine precipitate that
  5. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-051d7ae9b2294800992f014cd774d6f0
Source dataset
uspto-grants-2002_10
Patent number
US06458998B1

Reaction notes

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