Ammonia → HCID 22758138, compound

HRID 1287279Notes

Reaction equation

HRID 1287279 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH2:3]1.C(OCC)C.N.[Li]>C(O)C>[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH2:9][CH:10]=[CH:11][CH2:12][C:4]=2[CH2:3]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 4189657559-72-5HCID 3028194Lithium

Product 1

HCID 22758138HCID 22758138, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16.1 g. (0.10 mole) of 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene in 100 ml. of diethyl ether and 500 ml. of liquid NH3 is treated portionwise with 15 g. of lithium in small pieces. After 10 minutes, the mixture is treated dropwise with absolute ethanol to completely discharge the color. After removal of NH3, the residue is cooled and treated with water. Further extraction with ether and removal of organic solvent leaves crude 6-amino-1,4,6,7,8,9-hexahydro-5H-benzocycloheptene which is converted to its N-benzoyl derivative with benzoyl chloride-pyridine and thence to the tetrol as described previously.

Workup

  1. customAfter removal of NH3
  2. temperaturethe residue is cooled
  3. additiontreated with water
  4. extractionFurther extraction
  5. customwith ether and removal of organic solvent

Sources & evidence

ORD record
ord-55cc190fc36b4f7681771676f9aa2d99
Source dataset
uspto-grants-1976_10
Patent number
US03984407

Reaction notes

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