Water → (+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde

HRID 346989노트

반응식

HRID 346989 반응식
I[CH3:2].Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:36])([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)[C:22]4[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=4)[CH:19]=3)[NH:14][C:13](=[O:37])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1.O>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].[OH-].[Na+].C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:36])([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)[C:22]4[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=4)[CH:19]=3)[N:14]([CH3:2])[C:13](=[O:37])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 6328Methyl iodideHCID 21082104(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde monohydrochloride

생성물 1

HCID 10299684(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde수율 32%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

BTEAC (0.00395 mol), then iodomethane (0.00474 mol) were added to a solution of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5yl)methyl]benzaldehyde monohydrochloride (described in Example B1) (0.00395 mol) in NaOH (1N) and THF (20 ml). The mixture was stirred at room temperature for 18 hours, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.87 g) was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 0.61 g (32%) of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehyde, mp. 208° C.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.2; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue (0.87 g) was crystallized from diethyl ether
  10. filtrationThe precipitate was filtered off
  11. customdried

출처 및 근거

ORD 기록
ord-df411440408a42dba154584c8840f70d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173040B2

반응 노트

불러오는 중…