Hydrochloric Acid → HCID 67517935, compound

HRID 2173372Notes

Reaction equation

HRID 2173372 reaction equation
[N:1]1([C:6]2[CH:15]=[CH:14][C:13]3[CH:12]([C:16]([O:18]C)=[O:17])[CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+].O.Cl>O1CCCC1>[N:1]1([C:6]2[CH:15]=[CH:14][C:13]3[CH:12]([C:16]([OH:18])=[O:17])[CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium Hydroxide2×HCID 67517946HCID 67517946, compound

Product 1

HCID 67517935HCID 67517935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylate (1.04 g, 4.01 mmol) and lithium hydroxide (0.202 g, 4.81 mmol) were stirred in a mixture of tetrahydrofuran (10 ml)/water (10.00 ml) for 75 mins. The tlc showed some 20% starting material so more LiOH (50 mg, 1.19 mmol) was added and stirred for another 1 hr. The reaction was adjusted with 2N HCl (3 ml, 6 mmol) to pH 4-5 then extracted with ethyl acetate 2×. The ethyl acetate layers were combined and dried over Na2SO4, filtered and evaporated to dryness to yield 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylic acid. 1H-NMR (600 MHz, CDCl3): δ ppm 9.53 (s, 1H), 7.85-7.89 (q, 2H), 3.945 (t, J=5.46 Hz, 1H), 3.01-3.05 (m, 1H), 2.90-2.96 (m, 1H), 2.29-2.44 (m, 1H), 2.04-2.13 (m, 2H), 1.95-2.01 (m, 1H); LC-MS: (M+1)-28=218.

Workup

  1. additionwas added
  2. extractionthen extracted with ethyl acetate 2×
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-aa7fa4f7393c4bacb526c561370d9ef9
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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