Sodium Hydroxide → HCID 9886184, compound

HRID 726463Notes

Reaction equation

HRID 726463 reaction equation
[NH2:1][CH:2]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1)[C:3]([NH:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[CH:8][CH:7]=1)=[O:4].[OH-].[Na+]>C1COCC1>[NH2:1][CH:2]([C:22]1[CH:31]=[CH:30][C:29]2[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=2[CH:23]=1)[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:20][CH:21]=1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15817220HCID 15817220, compound

Product 1

HCID 9886184HCID 9886184, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.9 g (6.1 mmol) of the ester prepared in (e), 50 ml of THF and 150 ml of a methanolic sodium hydroxide solution (2N) were introduced into a round-bottomed flask and the mixture was heated at reflux for 2 hours. The reaction medium was evaporated to dryness, the residue taken up in water, and acidified to pH 5 with hydrochloric acid. The solids which had precipitated were filtered, washed with water and dried over P2 O5. 1.9 g (83%) of 4-[α-amino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoic acid of melting point 203°-204° C. were recovered.

Workup

  1. additionwere introduced into a round-bottomed flask
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hours
  4. customThe reaction medium was evaporated to dryness
  5. customThe solids which had precipitated
  6. filtrationwere filtered
  7. washwashed with water
  8. customdried over P2 O5
  9. custom1.9 g (83%) of 4-[α-amino-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoic acid of melting point 203°-204° C. were recovered

Sources & evidence

ORD record
ord-1b75e8f87b68442ba08425dec05b9199
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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