Hydrochloric Acid → 3-Aminomethyl-2-methyl-7-nitrobenzo[b]furan

HRID 342440Notes

Reaction equation

HRID 342440 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[CH2:14][N:15]1C(=O)C2=CC=CC=C2C1=O.O.NN.Cl>C(O)C>[NH2:15][CH2:14][C:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=2[O:6][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 701987382-Methyl-7-nitro-3-phthalimidomethylbenzo[b]furan

Product 1

HCID 702007853-Aminomethyl-2-methyl-7-nitrobenzo[b]furanYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-7-nitro-3-phthalimidomethylbenzo[b]furan (575 mg) and hydrazine monohydrate (172 mg) in ethanol (10 ml) was refluxed for 5 hours. The reaction mixture was cooled, acidified with 1N-hydrochloric acid and filtered. The filtrate was neutralized with aqueous saturated sodium bicarbonate and the ethanol in the mixture was evaporated in vacuo. The separated solid was collected, washed with water and dried to give 3-aminomethyl-2-methyl-7-nitrobenzo[b]furan (290 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe ethanol in the mixture was evaporated in vacuo
  5. customThe separated solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5e1328c63abf48b595d89d67d88f695a
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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