3-benzyloxy-2-nitro-N-methylaniline → 3-benzyloxy-N1-methylbenzene-1,2-diamine hydrochloride

HRID 2402555Notes

Reaction equation

HRID 2402555 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-])=O)=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[ClH:23]>[C].[Pt].C1(C)C=CC=CC=1>[ClH:23].[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([NH:12][CH3:13])[C:10]=1[NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 107298903-benzyloxy-2-nitro-N-methylanilineHCID 21887872Ethanol hydrochloride

Product 1

HCID 679540383-benzyloxy-N1-methylbenzene-1,2-diamine hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.80 g of 5% platinum carbon (dry) was added to a toluene (80 mL) suspension of 3-benzyloxy-N-methyl-2-nitroaniline (7.19 g, 27.8 mmol), and catalytic hydrogenation reaction was performed under ordinary pressure. The reaction solution was filtered to remove a catalyst, and the catalyst was washed with toluene (10 mL). The washing liquid was added to the precedent filtrate. A 1N hydrochloric acid ethanol solution (28 mL, 28.0 mmol) was added to the mixture under ice cooling, and the mixture was stirred under the same temperature for 30 minutes. The solvent was distilled off under reduced pressure at 20° C. or less. Precipitated crystals were collected by filtration, washed with toluene (15 mL), and dried at 40° C., thereby obtaining 6.30 g of an orange, crystal target compound (yield: 85%).

Workup

  1. filtrationThe reaction solution was filtered
  2. customto remove a catalyst
  3. washthe catalyst was washed with toluene (10 mL)
  4. additionThe washing liquid was added to the precedent filtrate
  5. distillationThe solvent was distilled off under reduced pressure at 20° C. or less
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washwashed with toluene (15 mL)
  9. customdried at 40° C.

Sources & evidence

ORD record
ord-e815e0b29aa44e35b34446f782c51bbc
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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