Ethyl cyanoacetate → 2-Oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 2416205Notes

Reaction equation

HRID 2416205 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([CH2:12][C:13](OCC)=[O:14])#[N:11].N1CCCCC1>CCO>[CH:7]1[CH:6]=[C:3]2[CH:4]=[C:12]([C:10]#[N:11])[C:13]([NH:1][C:2]2=[CH:9][CH:8]=1)=[O:14]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 682552-Aminobenzaldehyde

Product 1

HCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of o-aminobenzaldehyde (Sigma) (5.80 g, 48 mmol) in 250 mL of EtOH was added ethyl cyanoacetate (Aldrich) (6.20 mL, 58 mmol) followed by piperidine (Aldrich) (1.4 mL, 14 mmol) at RT. The reaction was heated at 75° C. for 15 h then cooled to RT. The solid was filtered, washed with EtOH and dried in vacuo to give a pale yellow crystalline solid. MS m/z: 171 (M+1); 169 (M−1).

Workup

  1. temperaturethen cooled to RT
  2. filtrationThe solid was filtered
  3. washwashed with EtOH
  4. customdried in vacuo
  5. customto give a pale yellow crystalline solid

Sources & evidence

ORD record
ord-568bc41906634def871d148fc265c99f
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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