Formaldehyde → HCID 22647937, compound

HRID 394163Notes

Reaction equation

HRID 394163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:23][CH2:22][NH:21][CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:32])[N:13]2[C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31].C=O.[C:35]([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:23][CH2:22][N:21]([CH3:35])[CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:32])[N:13]2[C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22647944HCID 22647944, compound

Product 1

HCID 22647937HCID 22647937, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(pyrrolidin-3-yloxy)-3,4-dihydroquinolin-2(1H)-one (0.046 g) in 5 mL of methanol was added formaldehyde (50 μL) and sodium cyanoborohydride (0.012 g). The reaction mixture was stirred for 48 h, then washed with 1N HCl (5 mL), extracted with 5×5 mL of ethyl acetate, washed with brine (5 mL), dried with sodium sulfate, and concentrated. Purification was achieved by preparative thin layer chromatography eluting with 10% ethanol/dichloromethane to yield product. Mass spectrum (ESI) 501.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.50-7.48 (m, 3H), 7.36-7.30 (m, 4H) 6.38 (s, 1H), 5.85 (s, 1H), 4.66 (m, 1H), 2.87-2.65 (m, 8H), 2.36 (s, 3H), 2.18-2.15 m, 1H), 1.94-1.91 (m, 1H).

Workup

  1. washwashed with 1N HCl (5 mL)
  2. extractionextracted with 5×5 mL of ethyl acetate
  3. washwashed with brine (5 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customPurification
  7. washeluting with 10% ethanol/dichloromethane
  8. customto yield product

Sources & evidence

ORD record
ord-601b891dfb0345abbce5c35e5f25d401
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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