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

HRID 570381Notes

Reaction equation

HRID 570381 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][CH3:31])(=[O:29])[CH2:25][C:26]([CH3:28])=O>CCOC(C)=O>[CH3:28][C:26]1[C:25]([C:24]([O:30][CH3:31])=[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 7757Methyl acetoacetateHCID 156812-Amino-5-nitrobenzophenone

Product 1

HCID 26609017Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylateYield 80%

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 (0.04 g, 041 mmol) and methyl acetoacetate (1.11 ml, 10.3 mmol) was stirred overnight at 120° C. under N2, than cooled to room temperature, diluted to 100 ml with EtOAc and washed with H2O. The organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by crystallization from EtOH to give pure product as a creamy solid (1.05 g, 80%). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=2.5 Hz, 1H), 8.48 (dd, J=2.5, 9.2 Hz, 1H), 7.53(m, 3H), 7.34(m, 2H), 3.59(s, 3H), 2.8(s, 3H).

Workup

  1. temperaturethan cooled to room temperature
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customfiltrate evaporated to dryness under reduced pressure
  6. customThe residue was purified by crystallization from EtOH

Sources & evidence

ORD record
ord-2057103ac4fa44a582aa7092f6b7487c
Source dataset
uspto-grants-2015_05
Patent number
US09023848B2

Reaction notes

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