Biphenyl → HCID 23498087, compound

HRID 1837335Notes

Reaction equation

HRID 1837335 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:19][CH:20]=[C:21]([C:27]#[N:28])[C:22](OCC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:15]=[C:14]2[C:12](=[CH:11][C:10]=1[F:16])[NH:13][CH:22]=[C:21]([C:27]#[N:28])[C:20]2=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 219518923-Fluoro-4-phenylmethoxyaniline

Product 1

HCID 23498087HCID 23498087, compoundYield 31.7%

Procedure

A mixture of 4-benzyloxy-3-fluoroaniline (6.06 g, 27.9 mmol) (U.S. Pat. No. 5,622,967) and ethyl (ethoxymethylene)cyanoacetate (5.08 g, 30.0 mmol) is heated at 120° C. for 45 minutes then cooled to room temperature. This solid is added in portions to a 3:1 mixture of diphenyl ether:biphenyl at 245° C. This mixture is heated at 245° C. for 3 hours then cooled and the solids are collected by filtration, washing with hexane and diethyl ether to provides 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4-dihydro-3-quinolinecarbonitrile, mp>250° C.

Workup

  1. customat 245° C
  2. temperatureThis mixture is heated at 245° C. for 3 hours
  3. temperaturethen cooled
  4. filtrationthe solids are collected by filtration
  5. washwashing with hexane and diethyl ether

Sources & evidence

ORD record
ord-5cbc41e2cc6d48ed9f00f0e923c18b37
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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