Hydrochloric Acid → HCID 10572373, compound

HRID 235082Notes

Reaction equation

HRID 235082 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]([C:6]1[C:10]([C@@H:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][C@H:12]2[N+:25]([O-])=O)=[C:9]([Si](C)(C)C)[S:8][CH:7]=1)=[O:5])[CH3:2].Cl>C(O)C.C(Cl)Cl.[Zn]>[CH2:32]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[C:10]([C@@H:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[CH2:14][CH2:13][C@H:12]2[NH2:25])=[CH:9][S:8][CH:7]=1)=[O:5])[CH3:33]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86750244HCID 86750244, compound

Product 1

HCID 10572373HCID 10572373, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 554 mg of trans-4-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalene-1-yl) -5-trimethylsilyl-3-thiophenecarboxylic acid, N,N-diethylamide, from step 2c above, in 8 mL of ethanol and 3 mL of 6 N HCl was added 700 mg of Zn dust, and the mixture was stirred for 15 min. The mixture was diluted with 20 mL of methylene chloride, then filtered. The organic layer of the flitrate was separated. The aqueous layer was adjusted to pH 10 and extracted with methylene chloride. The extract was dried over Na2SO4, filtered and concentrated. The residue was dissolved in 7 mL of methanol, 3 mL of 6N HCl was added, and the solution was stirred for 4 hours. The methanol was evaporated off, and the residue was dissolved in 6 mL of water, which was then extracted with ether. The aqueous layer was adjusted to pH 10 and extracted with ethyl acetate. Removal of the solvent gave 256 mg of the title product. MS 389 (M+H)+. NMR (CDCl3) δ:7.24 (d, 1 H, J=6 Hz), 6.93 (d, 1 H, J=6 Hz), 6.58 (s, 1H), 6.43 (s, 1H), 4.23 (d, 1H, J=10 Hz), 3.85 (s, 3H), 3.67 (s, 3H), 3.64 (m, 1H), 3.50-3.30 (m, 4H), 3.0-2.76 (m, 2H), 2.32-2.22 (m, 1H), 1.90-1.80 (m, 1H), 1.26-1.12 (m, 6H).

Workup

  1. filtrationfiltered
  2. customThe organic layer of the flitrate was separated
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 7 mL of methanol
  8. addition3 mL of 6N HCl was added
  9. stirringthe solution was stirred for 4 hours
  10. customThe methanol was evaporated off
  11. dissolutionthe residue was dissolved in 6 mL of water
  12. extractionwhich was then extracted with ether
  13. extractionextracted with ethyl acetate
  14. customRemoval of the solvent

Sources & evidence

ORD record
ord-fef6929e5f0d45f9bb0e99814556e58b
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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