Sodium Hydroxide → HCID 67094441, compound

Temperature

21 °C

3-Chloro-6-benzyloxy-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (1.33 g), methanol (27 ml) and 5M sodium hydroxide (27 ml) were refluxed for 2.5 hours. Methanol was evaporated and the resultant solid was filtered. The solid was dissolved in water and acidified with concentrated hydrochloric acid. The mixture was stirred in an ice-water bath, filtered and dried in vacuum. The resultant solid, copper (0.17 g) and quinoline (10.6 ml) were heated at 21° C. for one hour. To the cooled mixture was added 10% hydrochloric acid (26 ml) and dissolved in ethyl acetate. The solution was washed with 10% sodium carbonate and 1M hydrochloric acid and then it was evaporated to dryness. The residue, acetic acid (24 ml) and concentrate hydrochloric acid (3.2 ml) were refluxed 5 hours. The solution was evaporated to dryness. The residue was dissolved in diethyl ether and then extracted with 1M sodium hydroxide. The water phase was acidified with 6M hydrochloric acid and extracted into ethyl acetate. The solution was dried, evaporated to dryness and then triturated with diethyl ether and filtered.

1. customMethanol was evaporated
2. filtrationthe resultant solid was filtered
3. dissolutionThe solid was dissolved in water
4. filtrationfiltered
5. customdried in vacuum
6. additionTo the cooled mixture was added 10% hydrochloric acid (26 ml)
7. dissolutiondissolved in ethyl acetate
8. washThe solution was washed with 10% sodium carbonate and 1M hydrochloric acid
9. customit was evaporated to dryness
10. concentrationThe residue, acetic acid (24 ml) and concentrate hydrochloric acid (3.2 ml)
11. temperaturewere refluxed 5 hours
12. customThe solution was evaporated to dryness
13. dissolutionThe residue was dissolved in diethyl ether
14. extractionextracted with 1M sodium hydroxide
15. extractionextracted into ethyl acetate
16. customThe solution was dried
17. customevaporated to dryness
18. customtriturated with diethyl ether
19. filtrationfiltered

ORD record

ord-f8fb77d6a5c644769c38bd574e49e4d3

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318785B2