Acetic Acid → HCID 70980205, compound

HRID 1749079Notes

Reaction equation

HRID 1749079 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[N:8]=1)C.C(O)(=O)C>[Pd].CCO>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:9]1[CH:10]=[CH:11][C:12]2[NH:13][C:4](=[O:3])[CH2:5][O:6][C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70980720HCID 70980720, compound

Product 1

HCID 70980205HCID 70980205, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

[6-(2,4-Dimethoxy-benzylamino)-3-nitro-pyridin-2-yloxy]acetic acid ethyl ester (6.35 g, 16.2 mmol) and acetic acid (8 mL) were dissolved EtOH (160 mL). 10% Pd/C (635 mg) was added and the mixture was stirred under a hydrogen atmosphere for 24 hours after which time the product precipitated. The solid was collected by filtration, suspended in 1,4-dioxane (200 mL) and then heated briefly to ˜100° C. The mixture was allowed to cool and was then filtered while still luke-warm (to remove Pd/C). The filtrate was evaporated in vacuo to give 6-(2,4-dimethoxy-benzylamino)-1H-pyrido[2,3-b][1,4]oxazin-2-one (3.76 g) as a beige solid. MS: [M+H]+=316.

Workup

  1. customprecipitated
  2. filtrationThe solid was collected by filtration
  3. temperatureto cool
  4. filtrationwas then filtered
  5. temperaturewhile still luke-warm
  6. custom(to remove Pd/C)
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6079e0486a18440bb0217b131d1263a9
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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