Diphenyl Ether → HCID 178474057, compound

HRID 1432200Notes

Reaction equation

HRID 1432200 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([CH3:31])=[CH:26][C:27]([O:29]C)=O)=[CH:20][CH:19]=1)(=[O:16])[CH3:15]>>[OH:29][C:27]1[C:20]2[C:21](=[CH:22][CH:23]=[C:18]([NH:17][C:14](=[O:16])[CH3:15])[CH:19]=2)[N:24]=[C:25]([CH3:31])[CH:26]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 284013Methyl 3-{[4-(acetylamino)phenyl]amino}but-2-enoate

Product 1

HCID 178474057HCID 178474057, compoundYield 88%

Conditions

Temperature
252.5 °C

Procedure

Phenyl ether (1 L) was heated to 255° C. Butenoate 3 (334 g, 1.35 mol) was carefully added portionwise while maintaining temperature 245-260° C. After the addition was complete, the yellow-orange suspension was held at 255° C. for an additional 15 min. The mixture was slowly cooled to 40° C., the solids were collected by filtration and washed with EtOAc (3×500 mL) followed by MeOH (3×500 mL) to give hydroxy quinoline 4 as yellow-orange solid (256 g, 88% yield); 1H NMR (DMSO) δ 11.52 (br, s, 1H), 10.07 (s, 1H), 8.24 (s, 1H), 7.82 (d, 1H), 7.42 (d, 1H), 5.84 (s, 1H), 2.31 (s, 3H), 2.05 (s, 1H).

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was slowly cooled to 40° C.
  3. filtrationthe solids were collected by filtration
  4. washwashed with EtOAc (3×500 mL)

Sources & evidence

ORD record
ord-8ac2544ec2e4408ba37a5e9be67c38e1
Source dataset
uspto-grants-2009_11
Patent number
US07612080B2

Reaction notes

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