Ammonium formate → Methyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570382Notes

Reaction equation

HRID 570382 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-])=O)[CH:8]=2)[N:3]=1.C([O-])=O.[NH4+]>[Pd].CO.C1COCC1>[NH2:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 26609017Methyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

Product 1

HCID 68293887Methyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

10% palladium on carbon (0.22 g) was added to a solution of the product of Step 1 (1.05 g, 3.25 mmol) and ammonium formate (2.05 g, 32.5 mmol) in MeOH/THF mixture (1:1, 125 ml) under N2. The resulting mixture was stirred for 30 min at room temperature, filtered through Celite bed and filtrate evaporated to dryness. The residue was diluted to 50 ml with CH2Cl2, washed with H2O, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title product as a heavy oil (0.91 g, 98%), which was used in next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.86 (d, J=8.9 Hz, 1H), 7.44(m, 3H), 7.31(m, 2H), 7.13 (dd, J=2.5, 8.9 Hz, 1H), 6.61(d, J=2.5 Hz, 1H), 3.78(broad s, 2H), 3.53(s, 3H), 2.67(s, 3H).

Workup

  1. filtrationfiltered through Celite bed and filtrate
  2. customevaporated to dryness
  3. additionThe residue was diluted to 50 ml with CH2Cl2
  4. washwashed with H2O
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-ab4000306d064ce4a73a3db7f979e710
Source dataset
uspto-grants-2015_05
Patent number
US09023848B2

Reaction notes

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