Water → HCID 13983447, compound

HRID 580453Notes

Reaction equation

HRID 580453 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6](Cl)=[CH:7][CH:8]=2)[N:3]=1.[OH-].[K+].O.C(Cl)Cl.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][OH:24]>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:24][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 766463-(Dimethylamino)-1-propanolHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983447HCID 13983447, compound

Conditions

Temperature
60 °C

Procedure

A suspension of 2-amino-7-chloro-1,8-naphthyridine (89.75 g) in 3-dimethylamino-1-propanol (236 cc) is preheated to approximately 30° C. Potassium hydroxide pellets (85% pure; 65.8 g) are then introduced gradually. The reaction is exothermic, and the temperature rises to 80° C. at the end of the addition. The reaction mixture is then heated for a further 30 minutes to 90° C., allowed to cool to 60° C. and then poured into water (1500 cc) in the presence of methylene chloride (500 cc). The decanted organic extracts are washed with water (2×200 cc), dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (4 kPa). The product obtained in the form of an oil is crystallized by stirring in hexane (300 cc). The crystallized solid is then separated by filtration, washed with hexane and dried at 20° C. at reduced pressure (0.07 kPa). 2-Amino-7-(3-dimethylaminopropoxy)-1,8-naphthyridine (109 g), m.p. 88° C., is obtained.

Workup

  1. customis preheated to approximately 30° C
  2. additionare then introduced gradually
  3. additionthe temperature rises to 80° C. at the end of the addition
  4. temperatureThe reaction mixture is then heated for a further 30 minutes to 90° C.
  5. washThe decanted organic extracts are washed with water (2×200 cc)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness at 40° C. under reduced pressure (4 kPa)
  8. customThe product obtained in the form of an oil
  9. customis crystallized
  10. customThe crystallized solid is then separated by filtration
  11. washwashed with hexane
  12. customdried at 20° C. at reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-9f9b2bb4269d48dea229f9338c6804b3
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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