Hydrochloric Acid → 1,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5,8-dihydro-9-amino-5-ethyl-8-oxo-

HRID 525897Notes

Reaction equation

HRID 525897 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[C:10]3[O:13][CH2:14][O:15][C:9]3=[C:8]([N+:16]([O-])=O)[C:7]=2[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1)[CH3:2].Cl>C(O)(=O)C.[Pd]>[NH2:16][C:8]1[C:7]2[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:1][CH3:2])[C:12]=2[CH:11]=[C:10]2[O:13][CH2:14][O:15][C:9]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12478765HCID 12478765, compound

Product 1

HCID 30400661,3-Dioxolo(4,5-g)quinoline-7-carboxylic acid, 5,8-dihydro-9-amino-5-ethyl-8-oxo-Yield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 5-Ethyl-9-nitro-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (6 g, 19.59 mmol) and Pd/C (1 g, 0.940 mmol) in a mixture of acetic acid (150 mL) and con. HCl (50 mL) was hydrogenated on a Parr apparatus at 50 psi of H2 for 1 h at r.t. LCMS indicated completion of the reaction. The catalyst was filtered off. The filtrate was added dropwise into water (675 mL). The light yellow precipitates were collected by filtration, washed with water and dried in vacuo to afford 9-amino-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (4.72 g, 17.09 mmol, 87% yield). LCMS: (M+H)+: 277.2.

Workup

  1. customcompletion of the reaction
  2. filtrationThe catalyst was filtered off
  3. additionThe filtrate was added dropwise into water (675 mL)
  4. customThe light yellow precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6157172a0b91495190d13dff75e418d3
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…