Sodium Hydroxide → HCID 58551116, compound

HRID 2204284Notes

Reaction equation

HRID 2204284 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[O:13][C:14]3([CH2:19][CH2:18][N:17]([C:20]([C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=4[C:24]([O:26]C)=[O:25])=[O:21])[CH2:16][CH2:15]3)[C:5]=2[CH:4]=[N:3]1.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[O:13][C:14]3([CH2:19][CH2:18][N:17]([C:20]([C:22]4[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=4[C:24]([OH:26])=[O:25])=[O:21])[CH2:16][CH2:15]3)[C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58551660HCID 58551660, compound

Product 1

HCID 58551116HCID 58551116, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzoate (500 mg, 1.17 mmol), NaOH (5.0 mL of 1.0 M, 5.0 mmol), and 1,4-dioxane (5 mL) was heated at 80° C. for 1.5 h. The mixture was cooled to rt before it was concentrated in vacuo. The solid residue was taken up in water and was washed with ethyl acetate which was discarded. The aqueous layer was acidified with 1N HCl and was extracted with ethyl acetate (2×). The combined organics were washed with brine, dried over sodium sulfate, and were concentrated in vacuo to give 2-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzoic acid (33 mg, 75%) as a white solid. ESI-MS m/z calc. 403.2, found 404.2 (M+1)+; Retention time: 2.31 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 13.22 (s, 1H), 7.93 (d, J=7.7 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.65 (t, J=7.4 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 7.36 (br s, 2H), 7.28 (t, J=7.7 Hz, 1H), 7.08 (dd, J=13.8, 6.3 Hz, 2H), 4.39 (br s, 1H), 4.10 (s, 3H), 3.30-3.12 (m, 2H), 2.05-1.86 (m, 4H), 1.85-1.74 (m, 1H).

Workup

  1. temperatureThe mixture was cooled to rt before it
  2. concentrationwas concentrated in vacuo
  3. washwas washed with ethyl acetate which
  4. extractionwas extracted with ethyl acetate (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-aac311c8e3c444e8b1ffbc4cdbc4d086
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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