Hexane → HCID 22254471, compound

HRID 1611789Notes

Reaction equation

HRID 1611789 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[O:8]([CH2:15][CH2:16][NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][C:19]=1[NH2:28])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCCCCC>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][C:5]([NH:28][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:18]=1[NH:17][CH2:16][CH2:15][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:6]

Participants

5

Reactant 3

HCID 8058HexaneHCID 27597283-Methoxypropanoyl chlorideHCID 12114241HCID 12114241, compound

Product 1

HCID 22254471HCID 22254471, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-methoxypropanoyl chloride (0.86 ml, 7.9 mmol) was added dropwise over a 30 minute period to a chilled (ice bath) solution of N4-(2-phenoxyethyl)quinoline-3,4-diamine (2.0 g, 7.2 mmol) in dichloromethane (100 ml). After a few hours, a precipitate formed. The solvent volume was reduced under vacuum to near dryness and hexane (100 ml) was added. Vacuum filtration provided 2.9 g of 3-methoxy-N-{4-[(2-phenoxyethyl)amino]quinolin-3-yl}propanamide as a hydrochloride salt.

Workup

  1. waitAfter a few hours
  2. customa precipitate formed
  3. additionwas added
  4. filtrationVacuum filtration

Sources & evidence

ORD record
ord-ed8230a72975473da164590887f741a3
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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