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

HRID 915829Notes

Reaction equation

HRID 915829 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 18° C. 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-d187001222ef43e19143f7b31c2fdf78
Source dataset
uspto-grants-2007_09
Patent number
US07268143B2

Reaction notes

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