Acetic Acid → 2-(4-Cyano-benzyl)-3-hydroxy-7,8,9,10-tetrahydro-benzo[h]quinoline-4-carboxylic Acid

HRID 2375574Notes

Reaction equation

HRID 2375574 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH2:13][CH2:12][CH2:11][CH2:10][C:8]3=2)[C:3](=O)[C:2]1=[O:15].[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=O)COC(=O)C)=[CH:20][CH:19]=1)#[N:17].[C:32]([OH:35])(=[O:34])C>C(O)C.[OH-].[Na+]>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:2]([OH:15])=[C:3]([C:32]([OH:35])=[O:34])[C:4]3[C:9](=[C:8]4[CH2:10][CH2:11][CH2:12][CH2:13][C:7]4=[CH:6][CH:5]=3)[N:1]=2)=[CH:20][CH:19]=1)#[N:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 12339563Acetic Acid 3-(4-cyano-phenyl)-2-oxo-propyl EsterHCID 137804146,7,8,9-Tetrahydro-1H-benzo[g]indole-2,3-dione

Product 1

HCID 112220682-(4-Cyano-benzyl)-3-hydroxy-7,8,9,10-tetrahydro-benzo[h]quinoline-4-carboxylic AcidYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

In a 25 mL round-bottomed flask, 6,7,8,9-tetrahydrobenzo[g]indoline-2,3-dione (0.119 g, 0.590 mmol) was taken up in 1 mL ethanol and 3 mL 10 M NaOH, and the mixture heated at reflux temperature for 3 minutes. A solution of acetic acid 3-(4-cyano-phenyl)-2-oxo-propyl ester (0.167 g, 0.767 mmol) in 3 mL ethanol was then added and the reaction further heated for 10 minutes. The reaction mixture was then cooled to room temperature and acidified with glacial acetic acid, and the yellow precipitate collected by filtration. The procedure described above for the purification of example 7 was followed. Product was obtained as a bright yellow powder (42 mg, 20% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 1.74-1.87 (m, 4H) 2.83 (t, J=5.31 Hz, 2H) 3.12 (t, J=5.43 Hz, 2H), 4.40 (s, 2H), 7.28 (d, J=9.09 Hz, 1H) 7.51 (d, J=8.59 Hz, 2H) 7.75 (d, J=8.34 Hz, 2H) 8.23 (d, J=8.84 Hz, 1H).

Workup

  1. temperatureat reflux temperature for 3 minutes
  2. customthe reaction
  3. temperaturefurther heated for 10 minutes
  4. filtrationthe yellow precipitate collected by filtration
  5. customThe procedure described above for the purification of example 7

Sources & evidence

ORD record
ord-54a8668a1b9d4c40a3b9f49b26c10368
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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