4-Benzyloxy-2-chloro-7-methoxy-8-methylquinoline → HCID 178487709, compound

HRID 402153Notes

Reaction equation

HRID 402153 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[C:14]([CH3:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[C:11](Cl)[CH:10]=1)C1C=CC=CC=1.[CH:23]([C:26]1[CH:30]=[CH:29][NH:28][N:27]=1)([CH3:25])[CH3:24]>>[OH:8][C:9]1[C:18]2[C:13](=[C:14]([CH3:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[C:11]([N:28]2[CH:29]=[CH:30][C:26]([CH:23]([CH3:25])[CH3:24])=[N:27]2)[CH:10]=1

Participants

3

Reactant 2

HCID 576079364-Benzyloxy-2-chloro-7-methoxy-8-methylquinolineHCID 178439403HCID 178439403, compound

Product 1

HCID 178487709HCID 178487709, compoundYield 95%

Conditions

Temperature
155 °C

Procedure

A mixture of 4-benzyloxy-2-chloro-7-methoxy-8-methylquinoline (63, 1.00 g, 3.19 mmol) and 3-isopropylpyrazole was heated at 155° C. for 12 h. Then, the reaction mixture was partitioned between AcOEt and water, dried (Na2SO4) and evaporated. The residue was purified by column chromatography (AcOEt/CH2Cl2, 1:1) to give 900 mg (95%) of the target product 64 as a yellowish powder: m/z=298 (M+H)+.

Workup

  1. customThen, the reaction mixture was partitioned between AcOEt and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography (AcOEt/CH2Cl2, 1:1)

Sources & evidence

ORD record
ord-7d11626f12744357ac14411ff11dbf84
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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