Trifluoroacetic acid → 2,3-Dihydro-7-methyl-6-nitroindole

HRID 1275654Notes

Reaction equation

HRID 1275654 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:15]=2[CH3:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:17][C:15]1[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=[C:11]2[C:16]=1[NH:8][CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 158963701-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole

Product 1

HCID 158963682,3-Dihydro-7-methyl-6-nitroindoleYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole (5.00 g, 17.9 mmol), as prepared above (Example 1C), in methylene chloride (75 mL) is slowly added trifluoroacetic acid (15 mL). The reaction is stirred for 1.5 hours then partitioned between 200 mL of methylene chloride and 200 mL of 1 M aqueous sodium hydroxide solution. The methylene chloride layer is collected, dried over magnesium sulfate, filtered and evaporated to dryness on a rotary evaporator to afford 3.1 g of 2,3-dihydro-7-methyl-6-nitroindole as an orange solid (97% yield).

Workup

  1. customthen partitioned between 200 mL of methylene chloride and 200 mL of 1 M aqueous sodium hydroxide solution
  2. customThe methylene chloride layer is collected
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-4ef60e6d28b4408f9b62ca85d611a543
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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