Hydrochloric Acid → HCID 19823951, compound

HRID 728408Notes

Reaction equation

HRID 728408 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C(O)(=O)CC.Cl.[N:29]([O-])=O.[Na+].[CH3:33][N:34]([CH2:41][CH2:42][C:43]([OH:45])=[O:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[N+:1]([C:4]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:8]=[CH:7][C:5]=1[N:6]=[N:29][C:38]1[CH:39]=[CH:40][C:35]([N:34]([CH3:33])[CH2:41][CH2:42][C:43]([OH:45])=[O:44])=[CH:36][CH:37]=1)([O-:3])=[O:2]

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 1032Propionic AcidHCID 517045Sodium AcetateHCID 125224893-(Methylphenylamino)-propionic acidHCID 141221844-Dodecyl-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 19823951HCID 19823951, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Nitro-4-dodecylaniline (3.06 g) was dissolved in acetic acid (15 ml) and propionic acid (15 ml) and warmed whilst dilute hydrochloric acid (5 ml) was added. The mixture was cooled to 0° C. and sodium nitrite (0.7 g) was added at 0° C. The diazotised amine was then added to N-methyl-N-(2-hydroxycarbonylethyl)aniline (1.79 g) in water (100 ml) with dilute hydrochloric acid (3 ml). Sodium acetate was added until colour developed and the mixture was stirred for 0.5 hours. The crude product was recrystallised from CH2Cl2 to give a red solid (0.2 g).

Workup

  1. additionwas added
  2. customThe crude product was recrystallised from CH2Cl2

Sources & evidence

ORD record
ord-4deca5fba76847d99c067e762b2e0a36
Source dataset
uspto-grants-1991_09
Patent number
US05047516

Reaction notes

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