(3-Methyl-5-nitro-4-oxo-4H-quinolin-1-yl)-acetic acid ethyl ester → Ethyl (5-amino-3-methyl-4-oxoquinolin-1(4H)-yl)acetate

HRID 511535Notes

Reaction equation

HRID 511535 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:15]2[C:10](=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:19])[C:8]([CH3:20])=[CH:7]1)[CH3:2]>C(O)C.ClCCl.[Pd]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9](=[O:19])[C:8]([CH3:20])=[CH:7][N:6]2[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21]

Participants

5

Reactant 1

HCID 67256021(3-Methyl-5-nitro-4-oxo-4H-quinolin-1-yl)-acetic acid ethyl ester2×

Product 1

HCID 86654058Ethyl (5-amino-3-methyl-4-oxoquinolin-1(4H)-yl)acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (3-Methyl-5-nitro-4-oxo-4H-quinolin-1-yl)-acetic acid ethyl ester (Compound 301B, 250 mg, 0.86 mmol) in ethanol and dichloromethane (10 mL/20 mL) was cautiously treated with palladium on charcoal (10%) (30 mg) and hydrogenated at atmospheric pressure for 1 hr. The mixture was filtered and the filtrate was concentrated to a residue which upon trituration with t-butyl methyl ether gave the desired product as 150 mg of a light yellow solid (67%). 1H NMR of compound C (CDCl3, 300 MHz): δ 1.24 (t, 3H, J=7.5 Hz), 2.04 (s, 3H), 4.22 (q, 2H, J=7.5 Hz), 4.58 (s, 2H), 6.18 (d, J=8.4 Hz, 1H), 6.35 (d, J=8.5 Hz, 1H), 7.24 (m, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to a residue which upon trituration with t-butyl methyl ether

Sources & evidence

ORD record
ord-ca3c4f7ea8c94f92a85917f0f8c61499
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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