Phosphoric Acid → HCID 70607362, compound

HRID 1863117Notes

Reaction equation

HRID 1863117 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([NH:15][CH2:16][CH2:17][CH2:18][CH:19]([N:21]2C(=O)C3=CC=CC=C3C2=O)[CH3:20])=[C:9]2[C:4]=1[C:5]([CH3:33])=[CH:6][C:7]([CH3:32])=[N:8]2.NN.[P:36](=[O:40])([OH:39])([OH:38])[OH:37]>C(O)C>[P:36]([OH:40])([OH:39])([OH:38])=[O:37].[NH2:21][CH:19]([CH3:20])[CH2:18][CH2:17][CH2:16][NH:15][C:10]1[CH:11]=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[C:4]2[C:9]=1[N:8]=[C:7]([CH3:32])[CH:6]=[C:5]2[CH3:33]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 9321Hydrazine2×HCID 20393417HCID 20393417, compound

Product 1

HCID 70607362HCID 70607362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 5,6-dimethoxy-2,4-dimethyl-8-[(4-phthalimidopentyl)-amino]quinoline (12.7 g, 28 mmole) in ethanol (270 ml) containing 75% hydrazine (5.6 g, 84 mmole) was refluxed for 18 hr. An additional portion of 75% hydrazine (1.0 g, 15 mmole) was added and the mixture was refluxed for 1 hr more. Following the usual work-up, the base was isolated as a yellow-orange oil. The oil was dissolved in ethanol (30 ml) and treated dropwise with 0.90 equiv (27.8 ml) of 1 M phosphoric acid in ethanol. The phosphate salt separated initially as a gum, but dilution with ether (300 ml), seeding, and thorough trituration for several hours gave a uniform yellow solid, 11.5 g (90%), mp 163°-166°. Crystallization of the crude phosphate from methanol-ethanol-ether (1:1:2) afforded 82% recovery of product; mp 163°-166°.

Workup

  1. temperaturewas refluxed for 18 hr
  2. temperaturethe mixture was refluxed for 1 hr more
  3. customthe base was isolated as a yellow-orange oil
  4. customThe phosphate salt separated initially as a gum, but dilution with ether (300 ml)
  5. customthorough trituration for several hours gave a uniform yellow solid, 11.5 g (90%), mp 163°-166°
  6. customCrystallization of the crude phosphate from methanol-ethanol-ether (1:1:2)
  7. customafforded 82% recovery of product

Sources & evidence

ORD record
ord-9d9f44d9f050437aad5d5311aa757d6a
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

Loading…