Water → HCID 178473416, compound

HRID 711088Notes

Reaction equation

HRID 711088 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].O>N1C=CC=CC=1>[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 178497304HCID 178497304, compound

Product 1

HCID 178473416HCID 178473416, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-hydroxy-1H-indazole-6-carboxylate (1.6 g, 8.3 mmol) was suspended in pyridine (10 mL). Ethyl chloroformate (1.0 mL, 10 mmol) was added slowly and the reaction was allowed to stir at room temperature for 2 hours. The reaction was poured into water (65 mL) and cooled in a refrigerator for 4 hours. The resulting brown precipitate was collected by filtration, rinsed with water, and dried under vacuum to give the title compound (1.35 g, 61%) as a beige solid. +ESI (M+H) 265.0; 1H NMR (400 MHz, CDCl3, δ): 8.80 (d, J=6.0 Hz, 1H), 8.01 (dd, J=8.2, 1.2 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 4.60 (q, J=7.0 Hz, 2H), 3.98 (s, 3H), 1.57 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturecooled in a refrigerator for 4 hours
  2. filtrationThe resulting brown precipitate was collected by filtration
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7f09e2afd0784e7a8de372f9e6be7baf
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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