Hydrochloric Acid → HCID 69040269, compound

HRID 494178Notes

Reaction equation

HRID 494178 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=O.Cl.O>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 690401621-(3,4-Dihydro-7-nitro-1(2H)-quinolinyl)-2-methoxyethanone

Product 1

HCID 69040269HCID 69040269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-methoxyacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline (D6) (212 mg, 0.85 mmol) in dry THF (9 ml) at 0° C. under an argon atmosphere, was added borane/THF complex (4.5 ml, 4.5 mmol). The reaction was stirred at 0° C. for 0.5 h then ambient temperature for 3 h. 2M Hydrochloric acid (3 ml) was added cautiously followed by water (10 ml). The mixture was extracted with EtOAc (2×10 ml) which was dried over MgSO4 and concentrated in vacuo to give the desired product as an orange solid in quantitative yield. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.39 (m, 2H), 7.00 (m, 1H), 3.61 (dd, 2H), 3.52 (dd. 2H), 3.41 (m, 2H), 3.37 (s, 3H), 2.80 (t, 2H), 1.95 (m, 2H).

Workup

  1. waitambient temperature for 3 h
  2. extractionThe mixture was extracted with EtOAc (2×10 ml) which
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64678620922942d8b8530e0c72490976
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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