4-Methoxybenzylamine → HCID 57456934, compound

HRID 2077012Notes

Reaction equation

HRID 2077012 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].COC1C=CC(C[NH2:30])=CC=1>CN(C=O)C.C(O)(C(F)(F)F)=O>[NH2:30][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 57456935Benzyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 57456934HCID 57456934, compoundYield 116.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
115 °C

Procedure

Benzyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 66b) (0.55 g, 1.75 mmol) was dissolved in DMF (8 mL) and 4-methoxybenzylamine (0.56 mL, 4.31 mmol) was added. The reaction was heated at 115° C. for 30 minutes, then cooled to room temperature and poured into ice water. The resultant precipitate was dissolved in 10 mL TFA and stirred at room temperature for 15 minutes, then the mixture was poured into ice water. The resultant precipitate was collected, dissolved in dichloromethane, dried over MgSO4, filtered and evaporated to give the crude benzyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (600 mg) which was used as this without further purification. MS 295 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. customThe resultant precipitate was collected
  3. dissolutiondissolved in dichloromethane
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-da3d3555ab9f4185bd40e31d934fa216
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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