HCID 19093003, compound → HCID 19093032, compound

HRID 487733Notes

Reaction equation

HRID 487733 reaction equation
O[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[N+:15]([O-])=O>[Pd].C(O)C>[CH3:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[NH2:15]

Participants

4

Reactant 1

HCID 19093003HCID 19093003, compound

Product 1

HCID 19093032HCID 19093032, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-hydroxymethyl-1-nitro-3,4,5-trimethoxybenzene (200 mg, 0.82 mmol) and 10% palladium on carbon (100 mg) in ethanol (4 ml) was hydrogenated at 20 psi overnight. The mixture was filtered through a Celite pad and washed with ethanol. The combined filtrate and washings were evaporated in vacuo to dryness. The residue was chromatographed over a silica gel column (2×20 cm) using toluene/ethyl acetate (2:1, v/v) as the eluent to give 2-methyl-3,4,5-trimethoxyaniline as brown crystals (hexane), 130 mg (80%) with mp 49-51 ° C. 1H-NMR (CDCl3): δ2.01 (3H, s, Me), 3.49 (2H, b, exchangeable, NH2), 3.77, 3.78, and 3.82 (each 3H, s, 3×OMe), 6.07 (1H, s, H-6). Analyses: Calculated for C10H15NO3 : C, 60.90; H, 7.67; N, 7.10. Found: C, 61.05; H, 7.46; N, 7.00.

Workup

  1. customwas hydrogenated at 20 psi overnight
  2. filtrationThe mixture was filtered through a Celite pad
  3. washwashed with ethanol
  4. customThe combined filtrate and washings were evaporated in vacuo to dryness
  5. customThe residue was chromatographed over a silica gel column (2×20 cm)

Sources & evidence

ORD record
ord-0cb2cc798cba418f98dd9b82d19c878f
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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