Ethyl 2-chloroacetoacetate → HCID 75076919, compound

HRID 1496900Notes

Reaction equation

HRID 1496900 reaction equation
F[B-](F)(F)F.[F:6][C:7]([F:18])([F:17])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]#[N:16])=[CH:11][CH:10]=1.[Cl:19][CH:20](C(C)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>N1C=CC=CC=1.O>[Cl:19][C:20](=[N:16][NH:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]([F:17])([F:18])[F:6])=[CH:14][CH:13]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 87119132HCID 87119132, compound

Product 1

HCID 75076919HCID 75076919, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
-5 °C

Procedure

4-Trifluoromethoxybenzenediazonium tetrafluoroborate (63) (4.33 g, 15.7 mmol) was added to a solution of ethyl 2-chloroacetoacetate (64) (2.35 g, 14.3 mmol) in pyridine (6 mL) and water (6 mL) at −5° C. The mixture was stirred at −5° C. for 0.5 h and the precipitate was filtered and washed with ice cold water. Recrystallisation from EtOH/water gave ethyl 2-chloro{[4-(trifluoromethoxy)phenyl]hydrazono}ethanoate (65) (3.977 g, 82%) as pale orange needles: mp 128-130° C.; 1H NMR [(CD3)2SO] δ 10.68 (s, 1H), 7.43 (d, J=9.2 Hz, 2H), 7.34 (d, J=9.2 Hz, 2H), 4.30 (t, J=7.1 Hz, 2H), 1.30 (q, J=7.1 Hz, 3H). APCI MS m/z 309, 311 [M−H]−.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with ice cold water
  3. customRecrystallisation from EtOH/water

Sources & evidence

ORD record
ord-390b6162ce1c47c4a03041564831dbb4
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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