4-Methoxybenzylamine → 4-Amino-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 44402Notes

Reaction equation

HRID 44402 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]#[N:14].COC1C=CC(C[NH2:22])=CC=1>CN(C=O)C>[NH2:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 27775104-Chloro-1,2-dihydro-2-oxoquinoline-3-carbonitrile

Product 1

HCID 52003124-Amino-2-oxo-1,2-dihydroquinoline-3-carbonitrileYield 25.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-chloro-2-oxo-1,2-dihydroquinoline-3-carbonitrile (example 72) (0.66 g, 3.23 mmol) was suspended in DMF (7 mL), and 4-methoxybenzylamine (0.94 mL, 7.26 mmol) was added. The reaction was heated at 100° C. for 1 hour and the DMF was removed under vacuum. The residue was dissolved in TFA (6 mL) and stirred at room temperature for 30 minutes and dichloromethane (10 mL) was added. The solid product that formed was collected, suspended in water and the solution stirred overnight. The solid was collected by filtration to give 4-amino-2-oxo-1,2-dihydroquinoline-3-carbonitrile (0.150 g, 25%) as a white solid. M.p.: >250° C. 1H NMR (400 MHz, DMSO-d6) δ7.19 (m, 2H), 7.57 (m, 1H), 7.88 (bs, 2H), 8.12 (d, J=7.6 Hz, 1H), 11.23 (s, 1H). MS 186 (MH+).

Workup

  1. customthe DMF was removed under vacuum
  2. dissolutionThe residue was dissolved in TFA (6 mL)
  3. additiondichloromethane (10 mL) was added
  4. customThe solid product that formed
  5. customwas collected
  6. stirringthe solution stirred overnight
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-cce9922a5f3b470095ed458999a01420
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

Loading…