2-Phenylindole → 3-Nitroso-2-phenyl-1H-indole

HRID 746817Notes

Reaction equation

HRID 746817 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:16]([O-])=[O:17].[Na+]>C(O)(=O)C.O>[N:16]([C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:17]

Participants

5

Reactant 2

HCID 136982-PhenylindoleHCID 23668193Sodium Nitrite

Product 1

HCID 3439763-Nitroso-2-phenyl-1H-indole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-phenylindole (27) (25 gm, 0.129 mol) in acetic acid (250 mL) was cooled to 180C and a solution of sodium nitrite (8 g, 0.115 mol) in water (10 mL) was added dropwise while keeping the temperature of the reaction at ca. 20° C. The resulting reaction was stirred for 30 min at room temperature then diluted with ice water (250 mL). The reaction mixture was was filtered and the solid was washed with water then recrystallized using methanol to provide Compound 28. Yield=27.5 gm (96.4%). ES-MS: 223.22 (M++1); NMR (DMSO-d6): 7.0 (m, 1H), 7.1 (m, 1H), 7.22 (m, 1H), 7.32 (m, 2H), 7.40 (m, 1H), 7.48 (m, 2H), 7.60 (m, 1H).

Workup

  1. customthe temperature of the reaction at ca. 20° C
  2. customThe resulting reaction
  3. filtrationThe reaction mixture was was filtered
  4. washthe solid was washed with water
  5. customthen recrystallized

Sources & evidence

ORD record
ord-c0927639e7d54a4988c5c6a95601d859
Source dataset
uspto-grants-2008_07
Patent number
US07393955B2

Reaction notes

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