Hydrochloric Acid → HCID 67706197, compound

HRID 235079Notes

Reaction equation

HRID 235079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C@@H:9]([C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[C@H:8]([N+:21]([O-])=O)[CH2:7][CH2:6]2.Cl>C(O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C@@H:9]([C:15]1[S:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[C@H:8]([NH2:21])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67706183HCID 67706183, compound

Product 1

HCID 67706197HCID 67706197, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1.52 g of trans-1,2,3,4-tetrahydro-6,7-dimethoxy-1-(5-methyl-2-thiophenyl)-2-nitro-naphthalene (4.5 mmol), from step 1c above, in 40 mL of 95% ethanol and 12 mL of 6 N HCl was added 2.97 g of Zn dust (45 mmol), added in four portions. The mixture was stirred at room temperature for 30 min, filtered, and the flitrate concentrated to half the original volume, then extracted with methylene chloride after addition of aqueous sodium bicarbonate solution. The organic extract was dried over Na2SO4 and concentrated to yield 1.35 g of the title product. MS (M+H)+ : 304. NMR (CDCl3) δ:6.70 (d, 1H, J=3 Hz), 6.60 (bs, 2H), 6.46 (s, 1H), 3.88 (d, 1H, J=8 Hz), 3.85 (s, 3H), 3.69 (s, 3H), 3.18 (m, 1H), 2.92-2.78 (m, 2H), 2.43 (s, 3H), 2.12-2.04 (m, 1H), 1.78-1.64 (m, 1H).

Workup

  1. additionadded in four portions
  2. filtrationfiltered
  3. concentrationthe flitrate concentrated to half the original volume
  4. extractionextracted with methylene chloride
  5. additionafter addition of aqueous sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b9e3a60645c64c1db956077398359112
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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