N-(2-Hydroxyethyl)ethylenediamine → HCID 13914700, compound

HRID 652610Notes

Reaction equation

HRID 652610 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:27][CH2:28][N:29]([CH2:37][CH2:38][OH:39])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:7]=[C:8]3[C:17]4[C:12](=[C:13]([O:18][CH2:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:14]=[CH:15][CH:16]=4)[C:11](=[O:26])[C:10]=1[C:9]=23.[NH2:40][CH2:41][CH2:42][NH:43][CH2:44][CH2:45][OH:46]>CC(O)C>[OH:46][CH2:45][CH2:44][NH:43][CH2:42][CH2:41][NH:40][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:27][CH2:28][N:29]([CH2:37][CH2:38][OH:39])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:7]=[C:8]3[C:17]4[C:12](=[C:13]([O:18][CH2:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:14]=[CH:15][CH:16]=4)[C:11](=[O:26])[C:10]=1[C:9]=23

Participants

4

Reactant 2

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 13914704HCID 13914704, compound

Product 1

HCID 13914700HCID 13914700, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6.0 g (11.2 mmol) of 5-chloro-2-[2-[(2-hydroxyethyl)(phenylmethyl)amino]ethyl]-7-(phenylmethoxy)anthra[1,9-cd]pyrazol-6(2H)-one (8) and 12.2 ml (121 mmol) of 2-(2-aminoethylamino)-ethanol was heated at 160° C. for 24 hr. The cooled mixture was diluted with 60 ml of 2-propanol then maintained at 0°-5° C. for several days. The precipitate was collected, washed with cold 2-propanol then diethyl ether, and dried at 60° C. under vacuum for 18 hours to give 4.1 g (60%) of 10, mp 134°-137° C., 97% pure by HPLC.

Workup

  1. temperaturethen maintained at 0°-5° C. for several days
  2. customThe precipitate was collected
  3. washwashed with cold 2-propanol
  4. dry with materialdiethyl ether, and dried at 60° C. under vacuum for 18 hours

Sources & evidence

ORD record
ord-9a2d80fe7247497c9bdcd9adaa15b7cd
Source dataset
uspto-grants-1987_06
Patent number
US04672129

Reaction notes

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