Benzene → HCID 22754787, compound

HRID 66372Notes

Reaction equation

HRID 66372 reaction equation
[N+:1]([C:4]1[N:9]=[C:8]2O[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:12][C:7]2=[CH:6][CH:5]=1)([O-])=O.[CH3:19][OH:20].[CH:21]1C=CC=CC=1.C=O>[Ni].C(O)(=O)C>[CH3:8][N:9]([CH3:21])[C:4]1[N:1]=[C:19]2[O:20][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:12][C:7]2=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 887MethanolHCID 22754786HCID 22754786, compound

Product 1

HCID 22754787HCID 22754787, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

5-Nitro-2-phenyloxazolo[5,4-b]pyridine (1.2 g.) in 75 ml. of methanol, 75 ml. of benzene, 5 ml. of acetic acid and 8 ml. of 37% formaldehyde solution was hydrogenated over 1.5 teaspoonsful of Raney nickel. The catalyst was removed by filtration and the filtrate was diluted with 10 ml. of water and basified with solid sodium bicarbonate. The mixture was concentrated to dryness. The residue was crystallized from ethyl acetate to give 5-dimethylamino-2-phenyloxazolo[5,4-b]pyridine, m.p. 127°-129° C.

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was diluted with 10 ml
  3. concentrationThe mixture was concentrated to dryness
  4. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c963129b3ea74bbfbdcf56afad6b9a5c
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

Loading…