Sulfamic Acid → Ethyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

HRID 570385Notes

Reaction equation

HRID 570385 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.NS(O)(=O)=O.[C:24]([O:30][C:31](C)(C)[CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=O>C(OCC)(=O)C>[CH3:28][C:26]1[C:25]([C:24]([O:30][CH2:31][CH3:32])=[O:29])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:1]=1

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 15538Tert-butyl acetoacetateHCID 156812-Amino-5-nitrobenzophenone

Product 1

HCID 966460Ethyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-amino-5-nitrobenzophenone (1 g, 4.1 mmol), H2NSO3H (40 mg) and tert-butyl acetoacetate (1.3 ml, 10.3 mmol) was stirred for 12 h at 120° C. under N2. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo to give a solid, which was recrystallised from EtOH to give a pale orange solid (1.05 g, 76%). 1H NMR (300 MHz, CDCl3) δ 8.41-8.5(m, 2H, 8.15 (d, J=9 Hz, 1H), 7.52-7.55(m, 3H), 7.3-7.4 (m, 2H), 2.82(s, 3H), 1.24(s, 9H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid, which
  6. customwas recrystallised from EtOH

Sources & evidence

ORD record
ord-bd79e290ebad483eb0855b9cddf8f4f3
Source dataset
uspto-grants-2015_05
Patent number
US09023848B2

Reaction notes

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