Triethylamine → 1-(4-Chlorophenyl)-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid ethyl ester

HRID 232153Notes

Reaction equation

HRID 232153 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5](Br)=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2].O1CCN([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=2)CC1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[C:24]2[CH2:25][CH2:26][CH2:27][CH2:28][C:23]=2[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:6]=1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 71443533Ethyl bromo[2-(4-chlorophenyl)hydrazinylidene]acetate

Product 1

HCID 145762181-(4-Chlorophenyl)-4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid ethyl esterYield 54.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of bromo-(4-chlorophenyl)hydrazonoacetic acid ethyl ester (18.24 g, 60 mmol) in toluene (390 ml) and 10.02 g (60 mmol) of morpholinocyclohexene (10.02 g, 60 mmol) was cooled to 0° C. and triethylamine (12.6 ml, 90 mmol) was added. The solution was reacted for 1.5 hours at 0° C. and at ambient temperature for 48 hours. Triethylamine hydrochloride was filtered, the filtrate was washed with 10% hydrochloric acid, dried and evaporated. The crude product was crystallized from methanol to yield pure title compound (10.04 g), m.p. 139°-140° C. (lit 139°-141° C.).

Workup

  1. customThe solution was reacted for 1.5 hours at 0° C. and at ambient temperature for 48 hours
  2. filtrationTriethylamine hydrochloride was filtered
  3. washthe filtrate was washed with 10% hydrochloric acid
  4. customdried
  5. customevaporated
  6. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-1ebcb62288a7410a804c6ee914d9ef2b
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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