1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178428840, compound

HRID 2415463Notes

Reaction equation

HRID 2415463 reaction equation
C(O[C:4](=[O:23])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1)[CH3:7])C.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCCCCCC>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:4]([OH:23])=[CH:5][C:6]([CH3:7])=[N:8]2)=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 69289967HCID 69289967, compound

Product 1

HCID 178428840HCID 178428840, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
250 °C

Procedure

3.67 g (11.8 mmol) of 3-(3-benzyloxy-phenylamino)-but-2-enoic acid ethyl ester were added dropwise within 20 minutes to 5.5 ml of Dowtherm A heated at 250° C. (metal bath temperature). The solution was stirred further 10 minutes at 250° C. (bath temperature), cooled to RT and then treated with 20 ml of heptane. The brown viscous oil that had formed was isolated and triturated with 45 ml of AcOEt. The brown solid obtained was filtered off by suction, washed with AcOEt and dried in a high vacuum to give 1.19 g (35%) of 7-benzyloxy-2-methyl-quinolin-4-ol. ISP mass spectrum, m/e: 266.3 (M+1 calculated for C17H15NO2: 266).

Workup

  1. temperaturecooled to RT
  2. customThe brown viscous oil that had formed
  3. customwas isolated
  4. customtriturated with 45 ml of AcOEt
  5. customThe brown solid obtained
  6. filtrationwas filtered off by suction
  7. washwashed with AcOEt
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-58c35639ed31437e95741d42c38739c3
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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