1-Hydroxy-2-naphthoic acid → HCID 20336194, compound

HRID 1706003Notes

Reaction equation

HRID 1706003 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=[O:13].[OH-:15].[Na+].Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:15][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:24])=[CH:4][C:3]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 68441-Hydroxy-2-naphthoic acidHCID 14798Sodium HydroxideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 20336194HCID 20336194, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

0.05 mole of 1-hydroxy-2-naphthoic acid was dissolved in 70 ml of DMF, and 10 ml of a 40% aqueous solution of sodium hydroxide was added dropwise to the solution while introducing nitrogen gas. Then, 0.05 mole of ethyl α-bromo-propionate was added dropwise and the mixture was agitated at 40° C. for 3 to 4 hours to effect reaction. After completion of the reaction, the reaction mixture was poured into ice-hydrochloric acid, and crystals were recovered by filtration and recrystallized from acetonitrile to obtain a compound having a melting point of 178° C. Then, 0.01 mole of 1-hydroxy-4-[1-(ethoxycarbonyl)-ethoxy]-2-naphthoic acid so obtained and 0.01 mole of N-(δ-2,4-di-tert-amylphenoxy)butylamine were dissolved in 60 ml of dry dioxane, and 0.01 mole of dicyclohexylcarbodiimide was added to the solution. The reaction was conducted at room temperature under agitation for 2 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and separated by column chromatography to obtain a compound having a melting point of 75° C. (the yield being 52%). From the results of the elementary analysis, it was confirmed that this compound was the compound (1) illustrated above.

Workup

  1. additionwhile introducing nitrogen gas
  2. customreaction
  3. customAfter completion of the reaction
  4. filtrationwere recovered by filtration
  5. customrecrystallized from acetonitrile
  6. customto obtain a compound

Sources & evidence

ORD record
ord-7f57f59e177541dd96052c599228e417
Source dataset
uspto-grants-1980_06
Patent number
US04205990

Reaction notes

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