Hydrochloric Acid → HCID 178496285, compound

HRID 1624706Notes

Reaction equation

HRID 1624706 reaction equation
[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]([F:19])=[CH:9][C:7]=1[NH2:8].Cl.[CH3:21][O:22][CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27].CC([O-])=O.[Na+].[OH-].[Na+]>O.CO>[F:5][C:6]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]([F:19])=[CH:9][C:7]=1[NH:8][N:1]=[C:25]([C:24](=[O:30])[CH2:23][O:22][CH3:21])[C:26]([O:28][CH3:29])=[O:27]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 580723362,5-Difluoro-4-(morpholin-4-yl)aniline

Product 1

HCID 178496285HCID 178496285, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (3.3 g, 48 mmol) in H2O (10 mL) was added dropwise at 0° C. to a mixture of 2,5-difluoro-4-morpholin-4-ylaniline (8.6 g, 40 mmol) and 6 M HCl aqueous solution (40 mL, 240 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (5.2 mL, 40 mmol) and NaOAc (14 g, 240 mmol) in MeOH (40 mL) pre-cooled at 0° C. The mixture was adjusted to pH 7 with 1 M NaOH aqueous solution (200 mL). The precipitate was collected by filtration, washed with water and dried at room temperature to give the title compound (9.51 g, 64% yield) as a red solid: LC-MS (ESD m/z 372 [M+H]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried at room temperature

Sources & evidence

ORD record
ord-f908aeb9d7104b939796ae75f3f38810
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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