Reaction equation
[OH:1][C:2]1(C(O)=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH2:3]1.[CH3:16][OH:17].C[O-:19].[Na+].[CH3:21][S:22]([NH:25][CH2:26][CH2:27]Cl)(=[O:24])=[O:23]>CN(C=O)C>[OH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][CH2:27][CH2:26][NH:25][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:3][C:4]=1[C:16]([OH:19])=[O:17]Participants
Procedure
41 g (0.2 mole) of 1,4-dihydroxynaphthoic acid was dissolved in 200 ml DMF, into which was added dropwise 80 g of a 28% methanol solution of sodium methoxide (0.4 mole) and bubbling nitrogen therethrough at room temperature. Then, while controlling the reaction temperature between 35°-40° C., 25.2 g (0.16 mole) of β-methanesulfonamidoethyl chloride was added and the mixture was stirred for 1 hour. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered. The crystalline product was purified by refluxing with methanol and, thus, 20.8 g of 1-hydroxy-4-(β-methanesulfonamidoethoxy)-2-naphthoic acid was obtained with a yield of 40%.
Workup
- custombubbling nitrogen
- customat room temperature
- custombetween 35°-40° C.
- additionFinally, the solution was poured into a mixture of 100 ml
- concentrationof concentrated (36%) hydrochloric acid and 500 ml of water
- customto separate a crystalline product, which
- filtrationwas filtered
- customThe crystalline product was purified
- temperatureby refluxing with methanol
Sources & evidence
- ORD record
- ord-442b48213faa4779bbc9a15ec0b1b7c8
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04228233
Linked notes
Loading…