Hydrochloric Acid → 4-Amino-3-cyanobenzophenone

HRID 841186Notes

Reaction equation

HRID 841186 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])#[N:2].Cl.C(OCC)(=O)C>C(O)C.ClCCl.[Fe]>[NH2:17][C:16]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10586886HCID 10586886, compound

Product 1

HCID 107753914-Amino-3-cyanobenzophenoneYield 15.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred refluxing mixture of 3-cyano-4-nitrobenzophenone (Method 6) (1.50 g) and iron powder (3.64 g) in ethanol (50 ml) was added dropwise over 0.5 hour a solution of concentrated hydrochloric acid (0.35 ml) in ethanol (14 ml) and reflux was maintained overnight. The hot mixture was filtered through diatomaceous earth and the reaction flask and diatomaceous earth pad was washed with three 50 ml portions of ethanol. The combined filtrate was evaporated to yield a tan solid. Chromatography (eluent 10% to 40% ethyl acetate gradient in dichloromethane) gave the title compound (0.21 g) as a tan solid. M.p. 158-160° C.;

Workup

  1. temperatureTo a stirred refluxing
  2. temperaturereflux
  3. temperaturewas maintained overnight
  4. filtrationThe hot mixture was filtered through diatomaceous earth
  5. washthe reaction flask and diatomaceous earth pad was washed with three 50 ml portions of ethanol
  6. customThe combined filtrate was evaporated
  7. customto yield a tan solid

Sources & evidence

ORD record
ord-cf2c4f3350814d9cad7ff546735c3a72
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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