Ethyl cyanoacetate → HCID 86683080, compound

HRID 1497265Notes

Reaction equation

HRID 1497265 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[C:18]([CH2:20][C:21](OCC)=[O:22])#[N:19].N1CCCCC1>C1(C)C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:20]([C:18]#[N:19])[C:21](=[O:22])[NH:1]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 254180(2-Amino-4-methoxyphenyl)(phenyl)methanone

Product 1

HCID 86683080HCID 86683080, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
300 °C

Procedure

A solution of (2-amino-4-methoxy-phenyl)-phenyl-methanone (400 mg, 1.76 mmol) and ethyl 2-cyanoacetate (239 mg, 225 μl) in toluene (6 ml) containing catalytic amounts of piperidine (15.0 mg, 17.4 μl) was pumped at a flow rate of 0.42 ml min−1 (residence time 40 min) through a steel reactor coil (volume=17 ml) that was heated to 300° C. The reaction mixture was evaporated to dryness and the remaining solid was triturated with CH2Cl2/heptane 2:1 for 3 h. The solid was filtrated off and washed two times with CH2Cl2/heptane 1:1 to give the title compound (140 mg, 29%) as off-white solid. MS (ESI): 277.4 (M+H)+.

Workup

  1. customwas pumped at a flow rate of 0.42 ml min−1 (residence time 40 min) through a steel reactor
  2. customThe reaction mixture was evaporated to dryness
  3. customthe remaining solid was triturated with CH2Cl2/heptane 2:1 for 3 h
  4. filtrationThe solid was filtrated off
  5. washwashed two times with CH2Cl2/heptane 1:1

Sources & evidence

ORD record
ord-26507afa0faa42afbdb06cb0029b17a0
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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