Methylamine → HCID 20746075, compound

HRID 2308088Notes

Reaction equation

HRID 2308088 reaction equation
[CH3:1][NH2:2].[CH3:3][C:4]1[N:5]([C:16]([O:18]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[CH:8][CH:7]=2>C1COCC1.CCOCC>[CH3:1][NH:2][C:16]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[CH:8][CH:7]=2)[CH:12]=[C:4]1[CH3:3])=[O:18]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 226036172-Methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indole

Product 1

HCID 20746075HCID 20746075, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 2.0 M solution of methylamine in THF (25 ml, 50 mmole) was added to a solution of 2-methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indole 1a (2.11 g, 6.2 mmole) in THF (240 ml). The resultant reaction mixture was stirred at ambient temperature for 4 hours prior to removal of the solvent by concentration, in vacuo. The residue obtained was partitioned between EtOAc (200 ml) and H2O (200 ml). The layers were separated and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic extracts were washed with sat'd NaHCO3 (150 ml), dried over Na2SO4 and concentrated, in vacuo, to give a yellow solid which was suspended in Et2O (35 ml), filtered and washed with Et2O (2×20 ml) to give 1.17 g (81%) of a pale yellow solid. 1H NMR (DMSO-d6): δ 8.52 (1H, q, J=4.5 Hz), 8.46 (1H, d, J=2.3 Hz), 8.03 (1H, dd, J=2.3, 9.1 Hz), 7.71 (1H, d, J=9.1 Hz), 6.62 (1H, s), 2.89 (3H, d, J=4.5 Hz), 2.51 (3H, s). Anal. Calcd. for C11H13N3O3: C, 56.65; H, 4.75; N, 18.02. Found: C, 56.56; H, 4.78; N, 17.82.

Workup

  1. customThe resultant reaction mixture
  2. customto removal of the solvent
  3. concentrationby concentration
  4. customThe residue obtained
  5. customwas partitioned between EtOAc (200 ml) and H2O (200 ml)
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with EtOAc (2×100 ml)
  8. washThe combined organic extracts were washed with sat'd NaHCO3 (150 ml)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated, in vacuo
  11. customto give a yellow solid which
  12. filtrationfiltered
  13. washwashed with Et2O (2×20 ml)

Sources & evidence

ORD record
ord-8dac2ba3694e4e729285a264ec0424d4
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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