Biphenyl → HCID 178469464, compound

HRID 1761521Notes

Reaction equation

HRID 1761521 reaction equation
C1(=O)CCCCCCC1.[C:10]1([NH:18][CH:19]=[C:20]([C:26]([O:28]CC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>>[OH:28][C:26]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]=12

Participants

6

Reactant 5

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 10403CyclooctanoneHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)2×HCID 67906256HCID 67906256, compound

Product 1

HCID 178469464HCID 178469464, compound

Procedure

A solution of 85 g of the mixture of cyclooctanone and diethyl N-(1-cyclooctenyl)-aminomethylenemalonate in 20 ml. of Dowtherm® (a eutectic mixture of diphenyl ether and biphenyl) is added to 380 ml. Dowtherm® at 250°-255° under nitrogen. The distillate is collected in a water separator. After 0.5 hour the mixture is cooled to room temperature and solvent is removed under reduced pressure. The residual solid is triturated with ether to give ethyl 5,6,7,8,9,10-hexahydro-4-hydroxycycloocta[b]pyridine-3-carboxylate, m.p. 219°-222°.

Workup

  1. additionis added to 380 ml
  2. customat 250°-255°
  3. distillationThe distillate is collected in a water separator
  4. customsolvent is removed under reduced pressure
  5. customThe residual solid is triturated with ether

Sources & evidence

ORD record
ord-7562c3726b964d43b3fcf1a28386eb5e
Source dataset
uspto-grants-1989_05
Patent number
US04826854

Reaction notes

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