Methane → 1,2,3,5,6,7-Hexahydro-s-indacen-4-amine

HRID 1276542Notes

Reaction equation

HRID 1276542 reaction equation
[CH2:1]1[C:12]2[C:4](=[C:5]([NH:13]C(=O)C)[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.C>C(O)C>[CH2:9]1[C:10]2[C:6](=[C:5]([NH2:13])[C:4]3[CH2:3][CH2:2][CH2:1][C:12]=3[CH:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 297MethaneHCID 1118Sulfuric AcidHCID 599519N-(1,2,3,5,6,7-Hexahydro-S-indacen-4-yl)acetamide

Product 1

HCID 112522851,2,3,5,6,7-Hexahydro-s-indacen-4-amineYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of N-(1,2,3,5,6,7-hexahydro-s-indacen-4yl)-acetamide (110 grams) in YY mL of 25% sulfuric acid was treated with enough ethanol to make a solution (ca YY mL). The resulting solution was heated to reflux for a period of 2 days. The resulting black solution was treated with charcoal at reflux, filtered hot and cooled to 0° C. The solution was then cautiously neutralized with 20% sodium hydroxide solution. The resulting slurry was then filtered and washed with water until the filtrate ran neutral. The tan solid was then isolated and dried in vacuo to give 80 grams of the title compound, m.p. 94.5-96.6° C., which was used without further purification. If necessary, the title compound can be recrystallized from methanol to afford a white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for a period of 2 days
  3. temperatureat reflux
  4. filtrationfiltered hot
  5. filtrationThe resulting slurry was then filtered
  6. washwashed with water until the filtrate
  7. customThe tan solid was then isolated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b936c01f255c4003804430cbb5f3284c
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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