Methyl 6-hydroxy-2-naphthoate → HCID 18702910, compound

HRID 2287947Notes

Reaction equation

HRID 2287947 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14]C)=[O:13])[CH:6]=[CH:5]2.C[O-].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33]Cl)[CH2:28][CH2:27]2)=[CH:22][CH:21]=1>CN(C=O)C.CO>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]4)[CH2:30][CH2:31]2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 390995Methyl 6-hydroxy-2-naphthoateHCID 10244284HCID 10244284, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 18702910HCID 18702910, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

2.11 g of methyl 6-hydroxy-2-naphthoate and 0.84 g of sodium methoxide are stirred under N2 at 40° C. for 30 min in 50 ml of DMF. 4.6 g of 4-(p-chlorophenyl)piperazinoethyl chloride are then added and the reaction mixture is stirred at 40° C. for 8 h. It is diluted with 350 ml of methanol and the precipitate which is deposited is filtered off with suction. It is dissolved in 80 ml of DMF and 10 ml of water, and the mixture is treated with 3.8 g of KOH and stirred at 100° C. for 10 h. The DMF is largely stripped off on a rotary evaporator, the residue is poured onto water and acidified, and the resulting precipitate is filtered off with suction. 2.5 g of 6-{2-[4-(4-chlorophenyl)-1-piperazinyl]ethoxy}-2-naphthoic acid are obtained; m.p. 197-199° C.

Workup

  1. filtrationthe precipitate which is deposited is filtered off with suction
  2. dissolutionIt is dissolved in 80 ml of DMF
  3. addition10 ml of water, and the mixture is treated with 3.8 g of KOH
  4. stirringstirred at 100° C. for 10 h
  5. customThe DMF is largely stripped off on a rotary evaporator
  6. additionthe residue is poured onto water
  7. filtrationthe resulting precipitate is filtered off with suction

Sources & evidence

ORD record
ord-2b5054c60561442a8a891c5bd390214d
Source dataset
uspto-grants-2000_07
Patent number
US06087304

Reaction notes

Loading…