Trifluoroacetic acid → 5-Nitro-2,3-dihydro-1h-isoindole trifluoroacetic acid salt

HRID 2412172Notes

Reaction equation

HRID 2412172 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=2)[CH2:7]1.C1(OC)C=CC=CC=1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[N+:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][NH:6][CH2:14]2)([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59382318HCID 59382318, compound

Product 1

HCID 666726205-Nitro-2,3-dihydro-1h-isoindole trifluoroacetic acid salt

Conditions

Temperature
120 °C

Procedure

2-(2,4-dimethoxy-benzyl)-5-nitro-2,3-dihydro-1H-isoindole (13 g) in TFA (18 ml) was treated with anisole (6 ml) then heated in a CEM microwave synthesiser at 120° C. (30 Watts) for 20 minutes (carried out batch wise, 6 times). The reaction mixture was evaporated in vacuo and the residue partitioned between DCM and water. The water layer was separated, washed with DCM (×3) then evaporated and re-evaporated with toluene/MeOH (×3) to give 9.8 g of 5-nitro-2,3-dihydro-1H-isoindole trifluoroacetic acid salt as a beige solid. 1H NMR (DMSO-d6) 9.85 (2H, br s), 8.32 (1H, d), 8.25 (1H, dd), 7.70 (1H, d), 4.68 (2H, s), 4.65 (2H, s).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue partitioned between DCM and water
  3. customThe water layer was separated
  4. washwashed with DCM (×3)
  5. customthen evaporated
  6. customre-evaporated with toluene/MeOH (×3)

Sources & evidence

ORD record
ord-df8677df739647c9bb5c885bba37561a
Source dataset
uspto-grants-2014_08
Patent number
US08816087B2

Reaction notes

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