Ammonia → 2-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetamide

HRID 517847Notes

Reaction equation

HRID 517847 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12](OCC)=[O:13])[C:6]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C:5]=3[C:4]=2[CH:3]=1.[NH3:22]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([NH2:22])=[O:13])[C:6]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 44159218Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate

Product 1

HCID 441598112-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetamide

Procedure

Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate (0.1 g, 0.35 mmol) was taken in 4 ml aqueous ammonia and heated at 120 deg C. for 5 min in microwave. The solid product precipitated out after the reaction was filtered through a Buchner funnel and washed with 10% sodium bicarbonate (10 ml×2) followed by demineralised water (10 ml×2) wash. Product was vacuum dried and was taken in 5 ml ethanolic HCl, stirred for 15 min, concentrated in vacuo to afford 38 mg of 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetamide as hydrochloride salt. 1H NMR (DMSO)HCl Salt 10.38 (bs, 1H), 7.67 (s, 1H), 7.58 (s, 1H), 7.43 (d, 1H), 7.38 (s, 1H), 7.18 (d, 1H), 4.79 (d, 2H), 4.62 (d, 1H), 4.21-4.31 (m, 1H), 3.68-3.81 (m, 1H), 3.42-3.53 (m, 1H), 3.04-3.14 (m, 2H), 2.96 (s, 3H).

Workup

  1. temperatureheated at 120 deg C
  2. customThe solid product precipitated out after the reaction
  3. filtrationwas filtered through a Buchner funnel
  4. washwashed with 10% sodium bicarbonate (10 ml×2)
  5. washwash
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f900d41df17d4a5f8910fbefc48efa34
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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