Sodium Hydroxide → Amino-naphthalen-2-yl-acetic acid

HRID 2420571Notes

Reaction equation

HRID 2420571 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[NH:15]C(=O)N[C:12]1=[O:17].[OH-:18].[Na+]>>[NH2:15][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([OH:17])=[O:18]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 11229868HCID 11229868, compound

Product 1

HCID 2772357Amino-naphthalen-2-yl-acetic acid

Procedure

A solution of 5-(2-naphthyl) hydantoin (10g., 44.5 mmole) in 10% sodium hydroxide solution (50 ml.) was heated under reflux for 18 hours. The solution was cooled, filtered, diluted and treated with concentrated hydrochloric acid to bring the pH to 5.0. The resulting solid was filtered off washed with water and added to 5N-hydrochloric acid (2 L.). Insoluble material was filtered off and the filtrate was taken to pH 5.0 with 40% sodium hydroxide solution. On standing, the amino-acid crystallised out as platelets (3.92 g.) m.p. 238°-240°, λλmax. (pH 6.0 phosphate) 225 (ε 51,700), 276 (ε 3,520), 268 nm. (ε 3,420).

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. additiondiluted
  5. additiontreated with concentrated hydrochloric acid
  6. filtrationThe resulting solid was filtered off
  7. washwashed with water
  8. additionadded to 5N-hydrochloric acid (2 L.)
  9. filtrationInsoluble material was filtered off
  10. customthe amino-acid crystallised out as platelets (3.92 g.) m.p. 238°-240°, λλmax

Sources & evidence

ORD record
ord-e6ee4a63379049dc94ca7b3de01996ac
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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