Thiophene → 1,2,3,4-Tetrahydro-6-amino-2-methylbenzofuro[3,2-c]pyridine

HRID 1274111Notes

Reaction equation

HRID 1274111 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2[O:8][C:9]3[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]=2[CH2:3]1.C(N(CC)CC)C.S1C=CC=C1>C1COCC1.[Pd]>[NH2:15][C:14]1[C:9]2[O:8][C:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C:4]=3[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 8471TriethylamineHCID 221203251,2,3,4-Tetrahydro-2-methyl-6-nitrobenzofuro[3,2-c]pyridine

Product 1

HCID 221203391,2,3,4-Tetrahydro-6-amino-2-methylbenzofuro[3,2-c]pyridineYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-2-methyl-6-nitrobenzofuro[3,2-c]pyridine (0.0215 mol) and triethylamine (2 g) in THF (200 ml) was hydrogenated with palladium-on-charcoal catalyst 10% (2 g) as a catalyst in the presence of thiophene 4% (2 ml). After uptake of H2 (3 equivalents), the catalyst was filtered off and the filtrate was evaporated, yielding 4.2 g 1,2,3,4-tetrahydro-6-amino-2-methylbenzofuro[3,2-c]pyridine (interm. 7).

Workup

  1. filtrationAfter uptake of H2 (3 equivalents), the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5fa8989e9b20477f9cc2dda69b087adf
Source dataset
uspto-grants-2000_12
Patent number
US06156757

Reaction notes

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