Hydrazine hydrate (1:1) → 4-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]benzamide

HRID 587834Notes

Reaction equation

HRID 587834 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:40]=[CH:39][C:16]([C:17]([NH:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([C:27]([F:36])([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29])=[CH:22][C:21]=2[CH2:37][CH3:38])=[O:18])=[CH:15][CH:14]=1.O.NN>C(O)C.O>[NH2:3][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([C:27]([F:36])([C:28]([F:29])([F:30])[F:31])[C:32]([F:33])([F:34])[F:35])=[CH:22][C:21]=2[CH2:37][CH3:38])=[O:18])=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866666164-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)-6-methylphenyl]benzamide

Product 1

HCID 866666174-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)-6-methylphenyl]benzamide (0.80 g) was dissolved in ethanol (20 ml). To the solution, hydrazine monohydrate (0.28 g) was added and the mixture was stirred under heating at 60° C. for 4 hours. After adjusting to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with a saturated sodium bicarbonate solution and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain 4-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl] benzamide as a crude product (0.63 g). Without further purification, the crude product was used for the next reaction.

Workup

  1. customAfter adjusting to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with a saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3d336e8d75cb4f429dc4caf8bffc8fcf
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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