Sodium Hydroxide → HCID 178524091, compound

HRID 2272053Notes

Reaction equation

HRID 2272053 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:31]=[CH:30][C:10]2[C@@H:11]3[C@H:16]([CH2:17][CH2:18][C:9]=2[CH:8]=1)[N:15]([C:19]([C:21]1[CH:29]=[CH:28][C:24]2[NH:25][CH:26]=[N:27][C:23]=2[CH:22]=1)=[O:20])[CH2:14][CH2:13][CH2:12]3)=[O:6]>O1CCCC1>[NH:25]1[C:24]2[CH:28]=[CH:29][C:21]([C:19]([N:15]3[C@@H:16]4[C@@H:11]([C:10]5[CH:30]=[CH:31][C:7]([C:5]([OH:6])=[O:4])=[CH:8][C:9]=5[CH2:18][CH2:17]4)[CH2:12][CH2:13][CH2:14]3)=[O:20])=[CH:22][C:23]=2[N:27]=[CH:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497109HCID 178497109, compound

Product 1

HCID 178524091HCID 178524091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous NaOH solution (15 mL) is added to a solution of cis-4-(1H-benzoimidazole-5-carbonyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-8-carboxylic acid methyl ester (1.60 g) in tetrahydrofuran (15 mL) at room temperature. The resulting solution is stirred at room temperature for 5 h. The solution is concentrated under reduced pressure and water (100 mL) is added to the residue. 1 M Aqueous hydrochloric acid (15 mL) is then added and the precipitate formed is separated by filtration. The precipitate is washed with water and diethyl ether and dried to afford the title compound as a solid. Yield: 1.24 g (80% of theory); LC (method 1): tR=2.09 min; Mass spectrum (ESI+): m/z=376 [M+H]+.

Workup

  1. concentrationThe solution is concentrated under reduced pressure and water (100 mL)
  2. additionis added to the residue
  3. addition1 M Aqueous hydrochloric acid (15 mL) is then added
  4. customthe precipitate formed
  5. customis separated by filtration
  6. washThe precipitate is washed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-9d49fb15299740c684b3cd0ab90a9a1e
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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