Benzene → HCID 22754787, compound

HRID 259560Notes

Reaction equation

HRID 259560 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-cb86912d8d4c4cdebfd7d8f4b48391b5
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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