Hydrochloric Acid → 5-benzyloxy-N1-methylbenzene-1,2-diamine hydrochloride

HRID 1430408Notes

Reaction equation

HRID 1430408 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-])=O)=[C:13]([CH:16]=1)[NH:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:20]>[C].[Pt].C1(C)C=CC=CC=1>[ClH:20].[CH2:1]([O:8][C:9]1[CH:16]=[C:13]([NH:14][CH3:15])[C:12]([NH2:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 679540515-benzyloxy-N-methyl-2-nitroaniline

Product 1

HCID 679539765-benzyloxy-N1-methylbenzene-1,2-diamine hydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 1140TolueneSolvent

Procedure

5% platinum carbon (2.15 g, water content: 53.1%) was added to a toluene (300 mL) suspension of 5-benzyloxy-N-methyl-2-nitroaniline (20 g, 77.4 mmol), and catalytic hydrogenation reaction was performed at 4 atm. The reaction solution was filtered to remove a catalyst. The catalyst was washed with 2-propanol (40 mL), and the washing liquid was added to the precedent filtrate. Under ice cooling, concentrated hydrochloric acid (6.6 mL, 77.4 mmol) was added to the mixture, and the mixture was stirred under the same temperature for 30 minutes. The resulting precipitated crystals were collected by filtration, then washed with 2-propanol (60 mL), and dried at 50° C., thereby obtaining 18.6 g of a light-pink, crystal target compound (yield: 91%).

Workup

  1. filtrationThe reaction solution was filtered
  2. customto remove a catalyst
  3. washThe catalyst was washed with 2-propanol (40 mL)
  4. additionthe washing liquid was added to the precedent filtrate
  5. customThe resulting precipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with 2-propanol (60 mL)
  8. customdried at 50° C.

Sources & evidence

ORD record
ord-3f0ff69801524622a736af5c67eb423f
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

Loading…