Water → HCID 59441786, compound

HRID 1014398Notes

Reaction equation

HRID 1014398 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2].[N:16]([O-:18])=[O:17].[Na+].O>C(O)(C(F)(F)F)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium Nitrite2×HCID 67316433HCID 67316433, compound

Product 1

HCID 59441786HCID 59441786, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 0° C. orange solution of (2S)-1-acetyl-2-methyl-5-(methyloxy)-2,3-dihydro-1H-indole (5.19 g, 25.3 mmol) in TFA (30 mL) was treated with NaNO2 (1.745 g, 25.3 mmol) portion wise. After 2 h more NaNO2 (800 mg, 11.6 mmol) was added. After 1 h the resulting mixture was poured into water (450 mL). The resulting slurry was filtered and the solids were washed with water. The solids were dissolved in CH2Cl2. The layers were separated, the organic layer was dried (Na2SO4) and concentrated to afford (2S)-1-acetyl-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a green solid (5.73 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.23 Hz, 3H), 2.22 (s, 3H), 2.76 (d, J=17.21 Hz, 1H), 3.45 (dd, J=17.03, 8.97 Hz, 1H), 3.89 (s, 3H), 4.58-4.78 (m, 1H), 7.35 (s, 1H), 8.41 (s, 1H); ESIMS (M+H)+=251.02.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washthe solids were washed with water
  3. dissolutionThe solids were dissolved in CH2Cl2
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f079fed6889464db09933d7da12bcd0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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