Dimethylformamide → HCID 18702907, compound

HRID 2287949Notes

Reaction equation

HRID 2287949 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH3:14])=[C:4]([C:15]([O:17]C)=[O:16])[CH:3]=1.[CH3:19][O-].[Na+].C([N:24]([CH2:27][CH2:28]Cl)[CH2:25][CH3:26])C.[OH-].[K+].CN([CH:35]=[O:36])C>CO>[CH2:27]([N:24]([CH2:25][CH3:26])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH3:14])=[C:4]([C:15]([OH:17])=[O:16])[C:3]=1[O:36][CH2:35][CH3:19])[CH3:28]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 13364Diethylaminoethyl chlorideHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 15508983HCID 15508983, compound

Product 1

HCID 18702907HCID 18702907, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

1.5 g (6.1 mmol) of methyl 4-hydroxy-6-methoxy-1-methyl-2-naphthoate and 0.49 g (9.1 mmol) of sodium methoxide are stirred at 40° C. under argon for 15 min in 25 ml of DMF. 1.4 g of diethylaminoethyl chloride are then added and the mixture is additionally stirred at 40° C. for 30 min. The DMF is stripped off on a rotary evaporator, the residue is taken up in dilute hydrochloric acid, and the mixture is extracted with ethyl acetate. The aqueous phase is rendered alkaline with sodium hydroxide solution and extracted with ethyl acetate again. After concentrating this extract, 1.8 g of crude methyl 4-diethylaminoethyloxy-6-methoxy-1-methyl-2-naphthoate are obtained, which is hydrolyzed directly to the acid by boiling for 2 hours with 1 g of KOH in 20 ml of methanol. After concentrating the reaction mixture, the residue is dissolved in 20 ml of water and acidified to pH 5.5 with concentrated hydrochloric acid, the product precipitating. 0.5 g of 4-diethylamino-ethyloxy-6-methoxy-1-methyl-2-naphthoic acid is obtained; m.p. 170° C.

Workup

  1. customThe DMF is stripped off on a rotary evaporator
  2. extractionthe mixture is extracted with ethyl acetate
  3. extractionextracted with ethyl acetate again
  4. concentrationAfter concentrating this extract, 1.8 g of crude methyl 4-diethylaminoethyloxy-6-methoxy-1-methyl-2-naphthoate
  5. customare obtained
  6. concentrationAfter concentrating the reaction mixture
  7. dissolutionthe residue is dissolved in 20 ml of water
  8. customthe product precipitating

Sources & evidence

ORD record
ord-8ac6426c9f04413ba139407313270c5f
Source dataset
uspto-grants-2000_07
Patent number
US06087304

Reaction notes

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