Hydrazine hydrate (1:1) → HCID 54361032, compound

HRID 1638933Notes

Reaction equation

HRID 1638933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:23])[C:5]([N:12]2C(=O)C3=CC=CC=C3C2=O)=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2.O.NN>CS(C)=O>[NH2:12][C:5]1[C:4]([F:23])=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][O:10]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15018969HCID 15018969, compound

Product 1

HCID 54361032HCID 54361032, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 10.05 g of 41D in 60 mL of DMSO was added 7.58 g of hydrazine hydrate. The mixture was heated to 65°-75° C. for 3 hours, cooled, and poured into ice-water. The mixture was extracted with 3 portions of ether. The ether layer was extracted with water, brine, and dried over MgSO4 to afford 5-amino-8-chloro-6-fluorochromane (41E) as a yellow oil which solidified on standing, m.p.: 47°-50° C.

Workup

  1. temperatureThe mixture was heated to 65°-75° C. for 3 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with 3 portions of ether
  4. extractionThe ether layer was extracted with water, brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4b09fad57fc9404cb0ad554dd4e6f29b
Source dataset
uspto-grants-1989_11
Patent number
US04881967

Reaction notes

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