HCID 19922455, compound → HCID 67809652, compound

HRID 1463652Notes

Reaction equation

HRID 1463652 reaction equation
N[C:2]1[C:15]([CH3:16])=[C:14]([CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.N([O-])=[O:19].[Na+]>Cl>[CH3:16][C:15]1[C:2](=[O:19])[C:3]2[C:12](=[CH:13][C:14]=1[CH3:17])[C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH:4]=2

Participants

4

Reactant 2

HCID 19922455HCID 19922455, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 67809652HCID 67809652, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Substituted fluorenones are prepared as follows: 1-bromofluorenone is prepared from 2,6-dibromobenzophenone (Rec. Trav. Chem., 32, 167). 2,4-Dibromobenzophenone yields 1,3-dibromofluorenone (Rec. Trav. Chem., 32, 173). Treating 9,9-Dichloro-2,7-dibromofluorene with PCl5 at 210°-220° C. yields 2,7-dibromofluorenone (Annalen der Chemie, 387, 156). Treating 2,9,9-trichlorofluorene with water yields 2-chlorofluorenone (Ber., 54, 2073). Preparation of 2-nitrofluorenone is described in (Rec. Trav. Chem., 48, 897); (Annalen der Chemie, 43, 65). 4-Nitrofluorenone is described by Morgan, J. Chem. Soc., 2696, 1926. 1,8-Dinitrofluorenone is described by Huntress, J. Am. Chem. Soc., 54, 827, (1932). Preparation of 2,5-dinitrofluorenone by nitration is described by Morgan, J. Chem. Soc., 1926, 2696. 1,4-dimethylfluorenone is prepared from 2,5-dimethylbenzophenone-2-diazonium sulfate and copper powder (Ber., 53, 1395). 2-Fluorofluorenone is prepared by treating the 2-diazonium salt of fluorenone with HBF4 and heating the tetrafluoroborate salt to 180° C. (Ber. 66, 46, S2 [1933]. 2-Chlorofluorenone is prepared from 4-chlorobiphenyl-2-carboxylic acid or from 4-chlorobiphenyl-2-carboxylic acid in conc. H2SO4 at 50° C. (J. Chem. Soc., 113, (1950). Heating 4-Bromobiphenyl carboxylic acid with conc. sulfuric acid produces 2-bromofluorenone (J. Chem. Soc., 113, (1938). Treatment of 1-aminofluorenone with nitrous acid and potassium iodide yields 1-iodofluorenone J. Am. Chem. Soc., 64, 2845, (1942). The treatment of 4-nitrobiphenyl carboxylic acid with H2SO4 yields 2-nitrofluorenone (J. Chem. Soc., 113, (1938), and 5-nitrobiphenyl carboxylic acid yields 3-nitrofluorenone (J. Chem. Soc., 70, 1492 [1948]). 7-Bromo-2-nitrofluorenone is produced from 9-bromofluorene and nitric acid (J. Chem. Soc., 1607, (1935). 2,5-dinitrofluorenone and 2,7-dinitrofluorenone are produced by nitric acid on fluorenone (J. Chem. Soc., 68 2489, [1946]). Treatment of 2-amino-3,4-dimethylbenzophenone with sodium nitrite in hydrochloric acid and warming the reaction yields 2,3-dimethylfluorenone (J. Chem. Soc., 63, 2564-2566 [1941]). Reacting 2-bromofluorenone with ammonium hydroxide in the presence of Cu(I)Cl yields 2-aminofluorenone (Bull. Soc. Chem. France, [4] 41 61). Dimethylsulfate reacts with 2-aminofluorenone to produce 2,2-dimethylamino fluorenone (Monats., 41, 209), and treatment with acetic anhydride produces 2-acetamido fluorenone (Monats., 41, 207). Treating 3-hydroxydiphenyl-2-carboxylic acid with H2SO4 produces 1hydroxy-fluorenone (Ber., 28, 113), and further reaction with methyliodide yields 1-methoxy fluorenone (J. fur prakt. Chem., 59 453). Prep of 4 cyanofluorenone is described (Ber., 47, 2825) and vacuum distillation of 2-cyanodiphenyl carboxylic acid chloride produce 4-cyanofluorenone (J. Chem. Soc., 3248, (1928). All other positional isomers may be prepared in a similar manner to those transformations described above.

Sources & evidence

ORD record
ord-75968efb189049dbb4f88ea1d465ce1b
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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