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

HRID 579468

反応式

HRID 579468 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fd2c5cdf448a4fdaaf8662ae7684b07b
出典データセット
uspto-grants-2015_05
特許番号
US09040714B2

関連ノート

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