Hexane → HCID 178466034, compound

HRID 276837Notes

Reaction equation

HRID 276837 reaction equation
C(O[C:4](=[O:19])[C:5]([C:17]#[N:18])=[CH:6][NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=1)C.CCCCCC>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:15]([O:14][C:11]1[N:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[N:7]=[CH:6][C:5]([C:17]#[N:18])=[C:4]2[OH:19])[CH3:16]

Participants

4

Reactant 2

HCID 8058HexaneHCID 69850080HCID 69850080, compound

Product 1

HCID 178466034HCID 178466034, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A sample of 2-cyano-3-(6-ethoxy-pyridin-3-ylamino)-acrylic acid ethyl ester was heated at 257-259° C. (internal temperature) in Dowtherm for 10-12 hrs under nitrogen. After cooling, the reaction mixture was poured into n-hexane. The black solid was collected, and treated with MeOH and CH2Cl2 mixture (1:5). The title compound (or tautomer) was collected and dried mass spectrum (electrospray, m/e): 215.9 (M+H); IR cm-1: 3063, 2226; H-NMR δ(DMSO-d6): 1.355 (3H, t, CH3), 4.412 (2H, q, CH2), 7.244 (1H, d, C7-H), 7.983 (1H, d, C8-H), 8.682 (1H, s, C2-H), 10.50 (1H, bs, OH).

Workup

  1. temperatureAfter cooling
  2. customThe black solid was collected
  3. additiontreated with MeOH and CH2Cl2 mixture (1:5)
  4. customThe title compound (or tautomer) was collected
  5. customdried mass spectrum (electrospray, m/e)

Sources & evidence

ORD record
ord-aca15010ec9b4596b5495c0666a81c7b
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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