Hydrochloric Acid → 1-(3-Methyl-4-nitrophenyl)pyrrolidin-3-ylamine

HRID 349134Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:15][CH2:14][CH:13]([NH:16]C(=O)C)[CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 90 °C

Procedure

24 g (0.0911 mol) of N-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]acetamide (1) are introduced into a solution containing 75 ml of 37% hydrochloric acid and 165 ml of water in a 500 ml three-necked flask. The reaction medium is heated at 90° C. for 2 hours 30 minutes. After cooling, the medium is neutralized carefully with 75 ml of aqueous 35% sodium hydroxide (pH=approximately 8). The resulting solid is then filtered off, after which-it is washed with water until the washing waters are neutral. The product is then dried under vacuum over P2O5. 16.8 g (83%) of 1-(3-methyl-4-nitrophenyl)pyrrolidin-3-ylamine (2) are thus obtained in the form of a yellow solid.

Workup

temperatureAfter cooling
filtrationThe resulting solid is then filtered off
washafter which-it is washed with water until the washing waters
dry with materialThe product is then dried under vacuum over P2O5

Sources & evidence

ORD record: ord-ffd44be34d0a40d1beec8cd0fe7a244b
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179301B2

Reaction notes

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