N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-beta-oxo-1,3-dioxane-5-propanamide → N-(5-AMINO-2-METHOXYPHENYL)-2,2,5-TRIMETHYL-beta-OXO-1,3-DIOXANE-5-PROPANAMIDE

HRID 892404Notes

Reaction equation

HRID 892404 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([NH:10][C:11](=[O:24])[CH2:12][C:13](=[O:23])[C:14]2([CH3:22])[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16][CH2:15]2)[CH:9]=1)([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([NH:10][C:11](=[O:24])[CH2:12][C:13](=[O:23])[C:14]2([CH3:22])[CH2:19][O:18][C:17]([CH3:20])([CH3:21])[O:16][CH2:15]2)[CH:9]=1

Participants

4

Reactant 1

HCID 19895265N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-beta-oxo-1,3-dioxane-5-propanamide

Product 1

HCID 53685390N-(5-AMINO-2-METHOXYPHENYL)-2,2,5-TRIMETHYL-beta-OXO-1,3-DIOXANE-5-PROPANAMIDE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-β-oxo-1,3-dioxane-5-propanamide (22parts) are dissolved in dry tetrahydrofuran (250 parts) and placed in a Parr bottle. The nitro compound is hydrogenated at low pressure and at ambient conditions in a Parr apparatus over Pd-C catalyst (2.5 parts) for 3.5 hr. Thin layer chromatography is used to monitor reaction completion which appears to be quantitative with no other products except the desired amine. The reaction product is carried to the next synthesis without purification other than filtration to remove spent catalyst.

Workup

  1. customreaction completion which
  2. customThe reaction product is carried to the next synthesis without purification other than filtration
  3. customto remove

Sources & evidence

ORD record
ord-a80eaf050afc47a69fda9c2e28a7b3ba
Source dataset
uspto-grants-1992_06
Patent number
US05118599

Reaction notes

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