Ethyl cyanoacetate → HCID 178510524, compound

HRID 81019Notes

Reaction equation

HRID 81019 reaction equation
C(N(CC)CC)C.[O:8]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH2:24][C:25](=[O:33])[CH2:26][N+:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:34]([CH2:36][C:37](OCC)=[O:38])#[N:35]>CO>[C:34]([C:36]1[C@@H:19]([C:18]2[CH:21]=[CH:22][C:15]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:16][CH:17]=2)[C@H:26]([N+:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:25](=[O:33])[NH:24][C:37]=1[O-:38])#[N:35]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8471TriethylamineHCID 661394-PhenoxybenzaldehydeHCID 27564401-(Carbamoylmethyl)pyridinium Chloride

Product 1

HCID 178510524HCID 178510524, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (3.06 mL, 21.98 mmol) was added to a mixture of 4-phenoxybenzaldehyde (3.96 g, 19.98 mmol), 1-(2-amino-2-oxoethyl)pyridinium chloride (3.45 g, 19.98 mmol) and ethyl 2-cyanoacetate (2.260 g, 19.98 mmol) in methanol (80 mL) at room temperature. The resultant yellow solution was stirred at room temperature for 15 h to give a suspension. The yellow solid was collected by filtration, washed with methanol (2×20 mL), toluene (2×20 mL), hexanes (2×20 mL) and dried under vacuum to give trans-3-cyano-6-oxo-4-(4-phenoxyphenyl)-5-(pyridinium-1-yl)-1,4,5,6-tetrahydropyridin-2-olate (7.00 g, 91% yield). MS (ES+) m/z: 384 (M+H); LC retention time: 2.472 min (analytical HPLC Method A).

Workup

  1. customto give a suspension
  2. filtrationThe yellow solid was collected by filtration
  3. washwashed with methanol (2×20 mL), toluene (2×20 mL), hexanes (2×20 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-139eced270e540299616aea046f53f05
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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