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

HRID 2077017Notes

Reaction equation

HRID 2077017 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) δ 7.19 (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-a3955d150d0242fbb6822f1228257014
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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