Hydrochloric Acid → HCID 9925745, compound

HRID 1790289Notes

Reaction equation

HRID 1790289 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=[C:16]([N+:18]([O-])=O)[CH3:17].[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:27]>O1CCCC1.C(OCC)C>[ClH:27].[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][CH:16]([NH2:18])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 69621553HCID 69621553, compound

Product 1

HCID 9925745HCID 9925745, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from Step B (0.5 g, 1.83 mmol) was dissolved in tetrahydrofuran (50 mL). This solution was cooled to 0° C. and then a 1 M solution of lithium aluminum hydride in tetrahydrofuran (9 mL) was added. The reaction mixture was allowed to warm to room temperature and then warmed at reflux for an additional 5 h. The excess lithium aluminum hydride was destroyed by the addition of ethyl acetate and water. The organic material was extracted with dichloromethane (3×50 mL). The combined extracts were dried (MgSO4) and concentrated to give an oil which was dissolved in dry ethyl ether. To this solution was added a 1.0 M solution of hydrogen chloride in diethyl ether (10 mL). A solid formed (200 mg) and was collected by filtration: 1H NMR (DMSO-d6) δ 1.15 (d, 3H, CH3), 2.97 (m, 2H, CH2), 3.60 (m, 1H), 3.82 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 6.85 (s, 1H, Ar—H), 7.96 (d, 2H, Ar—H), 8.12 (d, 2H, Ar—H), 8.15 (bs, NH3+); MS 246 (M+1). Analysis. Calcd. for C15H19NO2.HCl.2 H2O: C, 63.13; H, 7.20; N, 4.91. Found: C, 62.73; H, 7.03; N, 4.87.

Workup

  1. temperatureto warm to room temperature
  2. temperaturewarmed
  3. temperatureat reflux for an additional 5 h
  4. customThe excess lithium aluminum hydride was destroyed by the addition of ethyl acetate and water
  5. extractionThe organic material was extracted with dichloromethane (3×50 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil which
  9. customA solid formed (200 mg)
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a8b3689f37c24bc3bfcb44a80276c1aa
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

Loading…