Potassium Hydroxide → HCID 59813780, compound

HRID 1925275Notes

Reaction equation

HRID 1925275 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:7][CH:6]=[CH:5]2.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1.[OH-].[K+]>CN(C=O)C.N1C=CC=CC=1.C(Cl)Cl.O.[Cu]>[CH3:38][N:37]([CH3:39])[CH2:36][CH2:35][O:34][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([NH:12][C:13](=[O:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:7][CH:6]=[CH:5]4)=[CH:23][CH:24]=[N:25]2)=[CH:30][C:29]=1[O:32][CH3:33]

Participants

9

Reactant 3

HCID 14797Potassium HydroxideHCID 67520279N-(6-Hydroxy-naphthalen-1-yl)-benzamideHCID 67520397HCID 67520397, compound

Product 1

HCID 59813780HCID 59813780, compound

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwaveable vial containing 0.300 g (1.1 mmol) of N-(6-hydroxy-naphthalen-1-yl)-benzamide in 1.5 mL DMF and 1.5 mL pyridine, was added 0.771 g (2.8 mmol) of [2-(4-chloro-6-methoxy-quinolin-7-yloxy)-ethyl]-dimethylamine. Then added (5 mmol %) copper grind into the mixture, along with 0.158 g (2.5 mmol) KOH pellets. The vial was heated in a microwave for 18 min at 120° C. (60 Watts constant power, CEM powermax). The mixture was diluted with CH2Cl2 and water, then transferred to seperatory funnel. The organics were extracted 3× with CH2Cl2. The organic layers were combined, dried over Na2SO4, filtered, and concentrated in-vacuo. The crude was purified by reverse-phase HPLC. A tan oil was collected, which was titled product. MS (ESI pos. ion) m/z: 508 (M+H). Calc'd for C31H29N3O4−507.22.

Workup

  1. customtransferred to seperatory funnel
  2. extractionThe organics were extracted 3× with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe crude was purified by reverse-phase HPLC
  7. customA tan oil was collected

Sources & evidence

ORD record
ord-ce798ff8200f4ed4b7c7bcdd46dc86df
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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