Hydrazine hydrate (1:1) → HCID 617104, compound

HRID 2290656Notes

Reaction equation

HRID 2290656 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([N:26]3C(=O)C4=CC=CC=C4C3=O)[CH:6]=[C:7]([O:24][CH3:25])[C:8]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:3]=1.O.NN>C(O)C>[NH2:26][C:5]1[CH:6]=[C:7]([O:24][CH3:25])[C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)=[C:9]2[C:4]=1[N:3]=[C:2]([Cl:1])[CH:11]=[C:10]2[CH3:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 555082HCID 555082, compound

Product 1

HCID 617104HCID 617104, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-chloro-6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline (23.2 g, 45.2 mmol) in ethanol (900 mL) was treated with excess hydrazine hydrate (75%, 16.75 mL) and the mixture was refluxed with mechanical stirring for 3 hours. After cooling, the solids were collected and washed with CH2Cl2. The combined filtrate and washings were evaporated in vacuo to a small volume and dissolved in CH2Cl2 ( 500 mL). The solution was extracted with 20% KOH (3×200 mL), and with brine, dried (K2CO3) and evaporated in vacuo to an amber gum. Recrystallization from cyclohexane-ligroin (5:2, 500 mL) with charcoaling gave 15.4 g (89%) of 1st crop title compound, mp 133°-135° C. Further recrystallization did not change the melting point.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. customthe solids were collected
  4. washwashed with CH2Cl2
  5. customThe combined filtrate and washings were evaporated in vacuo to a small volume
  6. dissolutiondissolved in CH2Cl2 ( 500 mL)
  7. extractionThe solution was extracted with 20% KOH (3×200 mL)
  8. dry with materialwith brine, dried (K2CO3)
  9. customevaporated in vacuo to an amber gum
  10. customRecrystallization from cyclohexane-ligroin (5:2, 500 mL) with charcoaling

Sources & evidence

ORD record
ord-710dd19e121c485d9ee89f19994dec3b
Source dataset
uspto-grants-1986_10
Patent number
US04617394

Reaction notes

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