Hydrochloric Acid → 6-amino-5-chloro-2,3-dihydro-1H-inden-1-one

HRID 65931Notes

Reaction equation

HRID 65931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[CH2:6][CH2:5]2.Cl>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:14])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221190235-Chloro-6-nitro-1-indanone

Product 1

HCID 221190136-amino-5-chloro-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

114 Grams (2.01 moles) of iron powder are added to a solution of 134 g (0.64 mole) of 5-chloro-6-nitro-1-indanone in 1600 ml of ethanol, then 63.5 ml of concentrated hydrochloric acid are added dropwise, and the reaction mixture is boiled for 4 hours. The precipitate is filtered off with suction, and the product is precipitated from the hot filtrate by the addition of water, then suction-filtered and washed with water. The residue of the reaction mixture is boiled with chloroform, the filtrate is dried with Na2SO4 and is then concentrated to dryness, after which process a further amount of the product is obtained. The substance melts at a temperature of from 198° to 200° C., and after recyrstallization from ethanol the melting point is in the range of from 203° to 205° C.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. customthe product is precipitated from the hot filtrate by the addition of water
  3. filtrationsuction-filtered
  4. washwashed with water
  5. dry with materialthe filtrate is dried with Na2SO4
  6. concentrationis then concentrated to dryness
  7. customafter which process a further amount of the product is obtained
  8. custommelts at a temperature of from 198° to 200° C.
  9. customis in the range of from 203° to 205° C.

Sources & evidence

ORD record
ord-00ff11ea7dbf4d609aa9e3c853244d07
Source dataset
uspto-grants-1978_12
Patent number
US04129656

Reaction notes

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