Hydrogen Bromide → HCID 20373065, compound

HRID 1834363Notes

Reaction equation

HRID 1834363 reaction equation
P(Cl)(Cl)([Cl:3])=O.OCCN1C2C(=CC=CC=2)CC(O)C1.Br.[NH:21]([CH2:28][CH2:29]O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:31]([CH:33]1O[CH2:34]1)[Cl:32]>C(O)(C)C.C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:29][CH2:28][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:34][CH:33]1[CH2:31][Cl:32]

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 7835EpichlorohydrinHCID 24813Phosphorus oxychlorideHCID 31235N-(2-Hydroxyethyl)anilineHCID 20373057HCID 20373057, compound

Product 1

HCID 20373065HCID 20373065, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 184 ml. of phosphorus oxychloride in 180 ml. of chloroform is added dropwise, with stirring, to a solution of 235 g. of 1-(2-hydroxyethyl)-3-hydroxy-1,2,3,4-tetrahydroquinoline (an oil, hydrobromide, m.p. 167°), obtainable by dropwise addition of 2-anilinoethanol to a solution of epichlorohydrin in isopropanol, boiling for 4 hours, evaporating and heating the residue at 160° for 3 hours in diethylaniline/cyclohexanol, in 355 ml. of chloroform. The mixture is boiled for 2 hours more and cooled. Excess phosphorus oxychloride is decomposed by adding 600 ml. of water dropwise. The phases are separated and the aqueous phase is extracted several times with chloroform, washed with water until neutral and evaporated to give 1-(2-chloroethyl)-2-chloromethylindoline hydrochloride, an oil, which is converted directly to the free base, b.p. 132°-135°/0.05 mm.

Workup

  1. customevaporating
  2. temperatureheating the residue at 160° for 3 hours in diethylaniline/cyclohexanol
  3. waitThe mixture is boiled for 2 hours
  4. temperaturemore and cooled
  5. additionby adding 600 ml
  6. customThe phases are separated
  7. extractionthe aqueous phase is extracted several times with chloroform
  8. washwashed with water until neutral and
  9. customevaporated

Sources & evidence

ORD record
ord-3713410d1e224230b6f48cf4b394de64
Source dataset
uspto-grants-1978_01
Patent number
US04070357

Reaction notes

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