Sodium sulfide nonahydrate → HCID 86732835, compound

HRID 525970Notes

Reaction equation

HRID 525970 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-])=O)[C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>C(O)C.O>[NH2:18][C:9]1[C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=[C:13]2[C:8]=1[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5][N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 86732834HCID 86732834, compound

Product 1

HCID 86732835HCID 86732835, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Under N2, 1-cyclopropyl-6,7-dimethoxy-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (10 g, 29.9 mmol) was treated with sodium sulfide nonahydrate (71.9 g, 299 mmol) in a mixture of Ethanol (100 mL) and Water (100 mL) for 2 h at 100° C. LCMS showed completion of reaction. After cooling down, the mixture was poured into cold water and the solution was adjusted to pH 2. The yellow precipitate was collected by filtration, washed with water and dried to afford 5-amino-1-cyclopropyl-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (8.9 g, 29.2 mmol, 98% yield) as a yellow solid.

Workup

  1. customcompletion of reaction
  2. temperatureAfter cooling down
  3. filtrationThe yellow precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4fca75c63c4c4f38b713c79097a33e3b
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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