Thiophene → 3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-amine

HRID 1906883Notes

Reaction equation

HRID 1906883 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[CH2:10][CH2:9][C:8]=2[CH:21]=1)([O-])=O.S1C=CC=C1.[H][H]>CO.[Pd]>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[O:14][CH2:13][CH:11]1[CH2:10][CH2:9][C:8]2[CH:21]=[C:4]([NH2:1])[CH:5]=[CH:6][C:7]=2[O:12]1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 202110343,4-dihydro-6-nitro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyranHCID 178418361HCID 178418361, compound

Product 1

HCID 202110563,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 34 parts of 3,4-dihydro-6-nitro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran, 1 part of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 31 parts (100%) of 3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-amine as an oily residue (intermediate 10).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1b97e7eb946e48b5a3f0b99157d554ff
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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