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

HRID 346278Notes

Reaction equation

HRID 346278 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 thinlayer 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-9ce40d5d74d44604a111eaad969bfb87
Source dataset
uspto-grants-1991_10
Patent number
US05061705

Reaction notes

Loading…