Methanol → Methyl 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoate

HRID 2277395Notes

Reaction equation

HRID 2277395 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.[CH3:29]CN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.CO>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:21])([CH3:20])[C:17]([O:19][CH3:29])=[O:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 681940182-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoic acid

Product 1

HCID 68193885Methyl 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoic acid (3 g, 7.75 mmol), EDCI (1.8 g, 9.3 mmol) and HOAT (0.2 g, 1.6 mmol) in CH2Cl2 (60 mL) was added CH3OH (5 mL). The reaction mixture was stirred at room temperature for 1 hour and then diluted with 20 mL of CH2Cl2. The organic phase was separated, washed with water (20 mL) and concentrated in vacuo. The crude product was purified by a column chromatography on silica gel (PE/EtOAc=2:1) to afford the title compound as a yellow oil (3 g, 96.5%).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (20 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by a column chromatography on silica gel (PE/EtOAc=2:1)

Sources & evidence

ORD record
ord-3982c278b1874ed49afd207709b222b9
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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