Methanol → HCID 178511724, compound

HRID 572237Notes

Reaction equation

HRID 572237 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[C@@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:17][CH2:16]1.CO>C(Cl)Cl>[NH2:6][C@H:15]1[CH2:16][CH2:17][C@H:18]([O:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 178525746HCID 178525746, compound

Product 1

HCID 178511724HCID 178511724, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35 wt % Hydrazine hydrate (0.93 g, 10.1 mmol) was added to a solution of compound 5 (2.0 g, 5.1 mmol) in CH2Cl2 (50 mL) followed by MeOH (50 mL) at room temperature. The reaction mixture was allowed to stir overnight. The resulting white precipitates were filtered off and the solvent was removed in vacuo. The resulting white solids were dissolved in aqueous 1N HCl solution and washed with CH2Cl2. Aqueous layer was basified with excess 1N NaOH solution and then extracted with CH2Cl2. After drying with MgSO4, the solvent was evaporated affording crude trans-4-nitro-benzoic acid 4-amino-cyclohexyl ester 6 as a white solid (1.1 g, 89% yield), which was used in the next step without further purification. 1H NMR (DMSO-d6): δ 8.26 (dd, J=44 and 9 Hz, 4H), 6.72 (d, J=7 Hz, 2H), 5.08 (s, 1H), 2.00-1.36 (m, 9H).

Workup

  1. customThe resulting white precipitates
  2. filtrationwere filtered off
  3. customthe solvent was removed in vacuo
  4. dissolutionThe resulting white solids were dissolved in aqueous 1N HCl solution
  5. washwashed with CH2Cl2
  6. extractionextracted with CH2Cl2
  7. dry with materialAfter drying with MgSO4
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-64b51bb5b3a5479186186a98c7433eb3
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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