Hydrochloric Acid → N~1~-(3-Methylbutyl)benzene-1,2-diamine

Under cooling, o-nitroacetoanilide (7.2 g, 40 mmol), acetone (28 ml) and powdered potassium hydroxide (2.2 g, 39 mmol) were mixed, to which 1-bromo-3-methylbutane (6.0 g, 40 mmol) was added. After the mixture was refluxed for 5 hours, the precipitate was removed by filtration. The filtrate was concentrated in vacuo and was extracted with chloroform. The occurred oily substance (9.8 g, 39 mmol) was refluxed for concd. hydrochloric acid (39 ml, 390 mmol) for 3 hours. The resultant was extracted with chloroform and concentrated in vacuo to give oily substance (6.4 g, 30.7 mmol), which was added to a mixture of powdered iron (17.1 g, 306 mmol), ethanol (24.5 ml), water (6.2 ml) and concd. hydrochloric acid (0.3 ml, 300 mmol). After the mixture was refluxed for 1.5 hours, the product was treated as in a usual process to obtain the title intermediate.

1. temperatureUnder cooling
2. additionwas added
3. temperatureAfter the mixture was refluxed for 5 hours
4. customthe precipitate was removed by filtration
5. concentrationThe filtrate was concentrated in vacuo
6. extractionwas extracted with chloroform
7. temperatureThe occurred oily substance (9.8 g, 39 mmol) was refluxed for concd
8. extractionThe resultant was extracted with chloroform
9. concentrationconcentrated in vacuo
10. customto give oily substance (6.4 g, 30.7 mmol), which
11. temperatureAfter the mixture was refluxed for 1.5 hours
12. additionthe product was treated as in a usual process

ORD record

ord-b8f275e7053e47ab8991b037d19542a9

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04818761