4-Hydrazinobenzoic acid → 1-(4-Carboxyphenyl)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-pyrazoline

HRID 2259802Notes

Reaction equation

HRID 2259802 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]2([CH3:19])[CH3:18])=O.[NH:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)[NH2:21]>CN(C)C=O>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([N:20]2[CH2:2][CH2:3][C:4]([C:6]3[CH:15]=[CH:14][C:13]4[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:19])[C:8]=4[CH:7]=3)=[N:21]2)=[CH:30][CH:29]=1)([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 147265116-(3-Chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

Product 1

HCID 147265191-(4-Carboxyphenyl)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-pyrazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.8 g (10 millimoles) of 6-3-chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (for preparation see Example 9) and 1.5 g (10 millimoles) of 4-hydrazinobenzoic acid in 40 ml of dimethylformamide was stirred until the reaction was complete (check by thin-layer chromatography). The mixture was poured onto water and the resulting crystals were filtered off under suction and washed with water and ethanol. Drying gave 2.2 g of the title compound of melting point 276°-278° C.

Workup

  1. additionThe mixture was poured onto water
  2. filtrationthe resulting crystals were filtered off under suction
  3. washwashed with water and ethanol
  4. customDrying

Sources & evidence

ORD record
ord-fc0f04e9aaf5441a844f463583b1a789
Source dataset
uspto-grants-1995_12
Patent number
US05475017

Reaction notes

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