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Water → Methyl 4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylate

HRID 388056
Notes
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Reaction equation

HRID 388056 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=O)[O:27]C1C=CC=CC=1.[CH2:35]([NH2:37])[CH3:36].O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[NH:25][C:26]([NH:37][CH2:35][CH3:36])=[O:27])[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=2)[N:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 22936324Phenyl N-(2-chloro-4-(7-methoxy-6-methoxycarbonyl-4-quinolyl)oxyphenyl)carbamate

Product 1

HCID 22936875Methyl 4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylateYield 93%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

Phenyl N-(2-chloro-4-(7-methoxy-6-methoxycarbonyl-4-quinolyl)oxyphenyl)carbamate (1.92 g, 4.00 mmol) and 2 M ethylamine (tetrahydrofuran solution) (4 ml) were stirred in dimethylformamide (8 ml) at room temperature for 30 minutes. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and the drying agent was filtered out and the filtrate distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (1.60 g, 3.72 mmol, 93%) as white crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered out
  4. distillationthe filtrate distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Sources & evidence

ORD record
ord-e700ba1a794141bab1516765fd4a089a
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372981B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes