Hydrochloric Acid → HCID 21455146, compound

HRID 436028Notes

Reaction equation

HRID 436028 reaction equation
[H][H].[OH:3][CH2:4][CH2:5][C:6]1[C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH2:14])[CH:9]=[CH:10][C:11]=1[NH:12][CH3:13].C(=O)([O-])[O-].[Ca+2].[CH2:23]([OH:26])[CH2:24]Br.Cl>O>[OH:26][CH2:23][CH2:24][C:10]1[C:11]([NH:12][CH3:13])=[C:6]([CH2:5][CH2:4][OH:3])[C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH2:14])[CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 108982-BromoethanolHCID 21455148HCID 21455148, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21455146HCID 21455146, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The substitution of a hydrogen of the amine function in the meta position of the nitro group is easily accomplished in the following manner. A mixture of 0.086 mols (18.1 g) of (2'-hydroxyethyl)-1-amino-2-nitro-4-methylamino benzene with 110 cm3 of water and 6.25 g of calcium carbonate is brought to reflux. 0.124 mols (8.75 cm3) of glycol bromohydrine is then introduced drop by drop, while stirring. Reflux is maintained for an hour and a half and then the reaction mixture is cooled and acidified with hydrochloric acid. The crystallized hydrochlorate is then dried, redissolved in water, and brought to an alkaline pH by adding ammonia. Drying yields 16 g of (2'-hyroxyethyl)-1-amino-2-nitro-(2'-hydroxyethyl)-4-methylamino benzene which melts at 99° C.

Workup

  1. temperatureto reflux
  2. temperatureReflux
  3. temperatureis maintained for an hour
  4. temperaturea half and then the reaction mixture is cooled
  5. customThe crystallized hydrochlorate is then dried
  6. dissolutionredissolved in water
  7. additionby adding ammonia
  8. customDrying

Sources & evidence

ORD record
ord-1a95557945a247a8b4b88cc4b58ee40c
Source dataset
uspto-grants-1977_02
Patent number
US04007228

Reaction notes

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