Acetic Acid → HCID 59807049, compound

HRID 1922375Notes

Reaction equation

HRID 1922375 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15](=O)[CH3:16])[C:9](=[O:18])[CH2:8][CH2:7]2)([O-:3])=[O:2].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH3:16])[C:9](=[O:18])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 59807104HCID 59807104, compound

Product 1

HCID 59807049HCID 59807049, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-nitro-1-(2-oxopropyl)-3,4-dihydroquinolin-2(1H)-one (500 mg, 2.01 mmol) and pyrrolidine (333 μL, 4.03 mmol) in 10 mL 1,2-dichloroethane (DCE) was treated with acetic acid (228 μL, 4.03 mmol) followed by sodium triacetoxyborohydride (1.27 g, 6.03 mmol). The suspension was stirred at room temperature overnight then quenched with 10 mL 1N NaOH. The mixture was diluted with 15 mL H2O then extracted with 2×100 mL CH2Cl2. The combined organic fractions were rinsed with 50 mL H2O, dried over MgSO4, filtered and concentrated to give a yellow residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (595 mg, 97.5%). 1H-NMR (CDCl3) δ: 8.13 (dd, J=2.7, 9.0 Hz, 1H), 8.07 (d, J=2.7 Hz, 1H), 7.21 (d, J=9.0 Hz, 1H), 4.21 (dd, J=8.7, 14.1 Hz, 1H), 4.02 (dd, J=5.4, 14.4 Hz, 1H), 3.00 (t, J=7.2 Hz, 2H), 2.91-2.62 (m, 7H), 1.92-1.90 (m, 4H), 1.00 (d, J=6.3 Hz, 3H).

Workup

  1. customthen quenched with 10 mL 1N NaOH
  2. additionThe mixture was diluted with 15 mL H2O
  3. extractionthen extracted with 2×100 mL CH2Cl2
  4. washThe combined organic fractions were rinsed with 50 mL H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow residue which
  9. customA yellow oil was obtained (595 mg, 97.5%)

Sources & evidence

ORD record
ord-54a110a9a3794868a6eab61ba7f27ca9
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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