Hydrochloric Acid → HCID 23459801, compound

HRID 2287203Notes

Reaction equation

HRID 2287203 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[O:11][C:10]=2[C:9]([CH2:20][CH2:21][CH3:22])=[C:8]2[C:3]=1[C:4](=[O:23])[CH2:5][CH2:6][CH2:7]2.C(=O)(O)[O-].[Na+].[BH4-].[Na+].Cl>CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[O:11][C:10]=2[C:9]([CH2:20][CH2:21][CH3:22])=[C:8]2[C:3]=1[CH:4]([OH:23])[CH2:5][CH2:6][CH2:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23459800HCID 23459800, compound

Product 1

HCID 23459801HCID 23459801, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateSolvent

Procedure

6,7,8,9-Tetrahydro-5-hydroxy-4,6-dioxo-10-propyl-4H-naphtho-[2,3-b]pyran-2-carboxylic acid (158 mg; 0.5 mmole) was dissolved in 10 ml of a pH10 buffer made from sodium bicarbonate (0.65 g) sodium carbonate (1.32 g) in water (100 ml). Sodium borohydride (20 mg; 0.53 mmole=2.12 equivalents) was added and the solution was stirred for 1 hour at room temperature and then poured into dilute hydrochloric acid and the yellow solid was filtered off, washed with water and dried in a vacuum oven over phosphoric oxide to yield a pure sample of the title compound (120 mg; 75.5%) mp 245°-9°.

Workup

  1. filtrationthe yellow solid was filtered off
  2. washwashed with water
  3. dry with materialdried in a vacuum oven over phosphoric oxide

Sources & evidence

ORD record
ord-fa89b27f7adb45e4b53fb121f6dec6bd
Source dataset
uspto-grants-1981_05
Patent number
US04269854

Reaction notes

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