Dimethylformamide → 6-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

HRID 579468

반응식

HRID 579468 반응식
BrC1C(=O)[O:4][C:5]2[C:10]([C:11]=1C)=[CH:9][CH:8]=[C:7](O)[CH:6]=2.B(O)(O)O.[C:19]([O-:22])([O-])=O.[Na+].[Na+].[CH3:25][N:26]([CH:28]=[O:29])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:10]=[CH:11][C:25]2[NH:26][C:28](=[O:29])[CH:9]=[CH:8][C:7]=2[C:6]=1[CH:19]=[O:22]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7628Boric AcidHCID 10340Sodium CarbonateHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

생성물 1

HCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde수율 42%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
90 °C

실험 절차

Compound 1 (15 g, 46 mmol), the boric acid (8.7 g, 50.6 mmol), Pd(PPh3)4 (1.88 g, 2.3 mmol), Na2CO3 (12.1 g, 115 mmol) were added to DMF (250 mL). The reaction mixture was degassed with N2 for three times, and then heated to 90° C. for 16 h. After cooled to RT, the solvent was concentrated, the residue was dissolved in sat Na2CO3 (150 mL). The aqueous was washed with DCM (100 mL×4), and then acidified by con.HCl to pH to ˜4. The result precipitate was collected by filtration, triturated with hot EA (50 mL), afforded compound 2 (6.5 g, 42%) as yellow solid. 1HNMR (DMSO-d6, 400 MHz): δ 10.55 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.24 (s, 1H), 7.19 (d, J=4.0 Hz, 1H), 6.86 (s, 1H), 3.88 (s, 3H), 2.45 (s, 3H).

후처리

  1. customThe reaction mixture was degassed with N2 for three times
  2. temperatureAfter cooled to RT
  3. concentrationthe solvent was concentrated
  4. dissolutionthe residue was dissolved in sat Na2CO3 (150 mL)
  5. washThe aqueous was washed with DCM (100 mL×4)
  6. filtrationThe result precipitate was collected by filtration
  7. customtriturated with hot EA (50 mL)

출처 및 근거

ORD 기록
ord-fd2c5cdf448a4fdaaf8662ae7684b07b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040714B2

연결된 노트

불러오는 중…