Sulfuric Acid → 5-benzyloxy-N1-methylbenzene-1,2-diamine

HRID 1430409Notes

Reaction equation

HRID 1430409 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.S(=O)(=O)(O)O>[C].[Pt].CC(O)C>[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 1118Sulfuric AcidHCID 679540515-benzyloxy-N-methyl-2-nitroaniline

Product 1

HCID 679539775-benzyloxy-N1-methylbenzene-1,2-diamineYield 94.7%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

5% platinum carbon (0.50 g, (DRY)) was added to a 2-propanol (170 mL) suspension of 5-benzyloxy-N-methyl-2-nitroaniline (10.00 g, 38.7 mmol), and catalytic hydrogenation reaction was performed at ordinary pressure. The reaction solution was filtered to remove a catalyst. The catalyst was washed with 2-propanol (20 mL), and the washing liquid was added to the precedent filtrate. Under ice cooling, 97% sulfuric acid (1.06 mL, 19.3 mmol) was added to the mixture, and then the mixture was stirred under the same temperature for 30 minutes. The resulting precipitated crystals were collected by filtration, then washed with 2-propanol (40 mL), and dried at 40° C., thereby obtaining 9.07 g of a light-purple, crystal target compound (yield: 94.7%).

Workup

  1. filtrationThe reaction solution was filtered
  2. customto remove a catalyst
  3. washThe catalyst was washed with 2-propanol (20 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 (40 mL)
  8. customdried at 40° C.

Sources & evidence

ORD record
ord-c1617e0b284f494d9de7aa602731dd11
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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